Method for controlling harmful organisms in crops of useful plants

ABSTRACT

Method for controlling harmful organisms in genetically modified cotton plants which contain a gene derived from  Bacillus thuringiensis  which encodes and expresses an insecticidally active protein, which comprises applying an insecticisally effective amount of one or more compounds from the following groups and a-f, described herein, to the plants, to their seeds or propagation stock and/or to the area in which they are cultivated. 
     The method according to the invention makes it possible to reduce the application rate of crop protection agents which act synergistically with the transgenic plants, and also to increase and widen the efficacy of the transgenic plants, and therefore offers both economical and ecological advantages.

The invention relates to a method for controlling harmful organisms in crops of Bt cotton.

Genetically modified cotton plants which express toxins from Bacillus thuringiensis (Bt) and which are consequently resistant to attack by certain harmful insects are known and are increasingly employed in commercial agriculture (see, for example, U.S. Pat. No. 5,322,938).

Although cotton which is genetically modified in this way already has very good properties, there are still a number of problems, so that a wide scope for improvement still exists.

For example, Bt toxins are not effective against all important cotton pests (see, for example, Flint, H. M. et al. (1995) Southwestern Entomologist 20/3, 281-292), the efficacy is insufficient at a high infestation intensity (see, for example, EPA Hearing Docket OPP-0478 (1997) Plant Pesticides Resistance Management, The Agriculture Program, The Texas A&M University System, College Station, Tex. 77843), Bt-resistance or Bt-cross-resistance may occur (see, for example, Gould, F. et al. (1997) Proc. Natl. Acad. Sci. USA 94, 3519-3523 or Bauer, L. S. (1995) Florida Entomologist 78/3, 414), or particular parts of plants may differ considerably in their insecticidal activity (see, for example, Lozzia, G. C. and Rigamonti, I. E. (1996) Boll. Zool. agr. Buchic Ser II, 28/1, 51-69).

It was therefore another object to provide the most effective and environmentally compatible problem solutions possible for controlling pests of cotton. WO-A 97/45 017 describes a process for controlling Lepidoptera in Bt cotton where an insecticidally active benzoylurea derivative is additionally used. It is not possible to draw conclusions with respect to the activity of other classes of insecticides from this publication.

Surprisingly, it has now been found that certain classes of insecticides show synergistic effects when used in combination with Bt cotton.

The invention therefore provides a method for controlling harmful organisms in genetically modified cotton plants which contain a gene derived from Bacillus thuringiensis which encodes and expresses an insecticidally active protein, which comprises applying an insecticidally effective amount of one or more compounds from the following groups a-f to the plants, to their seeds or propagation stock and/or to the area in which they are cultivated:

a) Organophosphorus compounds:

triazophos (726), monocrotophos (502), methamidophos (479), chlorpyrifos (137), parathion (551), acephate (4), profenofos (594), malathion (448), heptenophos (395);

b) Pyrethroids:

tralomethrin (718), cypermethrin (183), cyhalothrin (179), (lambda)-cyhalothrin (180), deltamethrin (204), fenvalerates (319), (alpha)-cypermethrin (183/184), cyfluthrin (176), fenpropathrin (312), etofenprox (292);

c) Carbamates:

aldicarb (16), bendiocarb (56), carbaryl (106), carbofuran (109), formetanates (369), pirimicarb (583)

d) Biopesticides:

Bacillus thuringiensis (46, 47), granuloses and nuclear polyhedrosis viruses, beauveria bassiana (52), beauveria brogniartii (53), baculoviruses, such as autographa california;

e) Others:

endosulfan (270), abamectin (1), XDE-105 (754), diafenthiuron (208), fipronil (323), chlorfenapyr (123), tebufenocides (679), fenazaquin (301), imidacloprid (418), triazamates (724), fentin (317), amitraz (22), MK-242;

f) 4-Haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines of the formula (I), if appropriate also in the form of their salts,

where the symbols and indices have the following meanings:

Y is halo-C₁-C₆-alkyl;

X is CH or N;

m is 0 or 1;

Q is a 5-membered heterocyclic group

 in which

a) X¹ = W, X² = NR^(a), X³ CR^(b)R¹ or b) X¹ = NR^(a), X² = CR^(b)R¹, X³ = W or c) X¹ = V, X² = CR^(a)R¹ , X³ = NR^(b) or d) X¹ = V, X² = CR^(a)R², X³ = CR^(b)R³ or e) X¹ = V, X² = CR⁴R⁵, X³ = CR⁶R⁷ or f) X¹ = NR^(a), X² = CR^(b)R¹, X³ = NR⁸;

R^(a) and R^(b) together are a bond

V is oxygen, sulfur or NR⁹;

W is oxygen or sulfur;

R¹ is hydrogen,

(C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl,

(C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl,

where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

 halogen, cyano, nitro, hydroxyl, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰,

 —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰,

 —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂,

 —NRC¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂,

 —C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂,

 —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—N[C(═W)R¹⁰]₂, —N[(C═W)R¹⁰]—NR¹⁰ ₂,

 —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR¹⁰],

 —NR¹⁰—R¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰,

 —NR (C═NR¹⁰)NR¹⁰ ₂,

—O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —SO₂NR¹⁰ ₂, —NR SO₂R¹⁰,

—SO₂OR¹⁰, —OSO₂R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃,

—SeR¹⁰, —R¹⁰ ₂, —(═W)R¹⁰ ₂,

—SOR¹⁰, —SO₂R , —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, aryl and heterocyclyl,

the two last-mentioned radicals optionally being substituted by one or more radicals from the group

 (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, SiR¹⁰ ₃, —C(═W)R¹⁰, —C(═W)OR¹⁰, C(W)NR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, nitro, cyano and hydroxyl,

aryl,

which is optionally substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl, where these six abovementioned radicals are optionally substituted by one or more radicals from the group

 halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰,

 —C(═W)NR¹⁰ ₂, —OR¹⁰, NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and

 —SO₂R¹⁰,

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═NOR )R¹⁰,

—C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰,

—OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂,

—NR¹⁰C(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ _(3 , —PR) ¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂ and —PW₃R¹⁰ ₂,

heterocyclyl,

which is optionally substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl, where the six abovementioned radicals are optionally substituted by one or more radicals from the group

 cyano, nitro, halogen, —C(═W)R¹⁰, —C(═W)OR¹⁰,

 —C(═W)NR¹⁰ ₂, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂,

 —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰,

 —SOR¹⁰ and —SO₂R¹⁰,

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰,

—C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰,

—OR hu 10, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ ₁₀, —SO₂R¹⁰, —C(═W)R¹⁰,

—C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰,

—C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR OC(═W)R¹⁰,

—N[C(═W)R¹⁰]₂, —NR¹⁰, —(═W)OR¹⁰, —C(═W)NR¹⁰, —NR¹⁰ ₂,

—C(═W)R¹⁰, —NR¹⁰C[(═W)R¹⁰], —NR¹⁰—C(═W)R¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—NC(═W)R¹⁰ ₂, —N(C═W)R¹⁰—NR¹⁰ ₂,

—NR¹⁰, —NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR¹⁰], —NR¹⁰—NR¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰,

—NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰,

—SO₂NR¹⁰ ₂, —NR SO₂R¹⁰, —SO₂OR¹⁰, —OSO₂R¹⁰,

—SC(═W)R¹⁰, —SC(═W)OR¹⁰, —SC(═W)R¹⁰, —PR¹⁰ ₂, —PW₂R¹⁰ ₂,

—PW₃R¹⁰ ₂, SiR¹⁰ ₃ or halogen;

R² and R³ independently of one another have the definitions given in R¹;

R² and R³ together form a 5- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹;

R⁴ and R⁶ independently of one another have the definitions given in R¹;

R⁴ and R⁶ together form a 4- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹;

R⁵ and R⁷ independently of one another are hydrogen,

(C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl,

where the six last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰,

—C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰,

—OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂,

—NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂,

—C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂,

—NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—N[C(═W)R¹⁰]₂, —N[(C═W)R¹⁰]—NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR¹⁰],

—NR¹⁰—NR¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰,)R¹⁰,

—NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰,

—OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —SeR¹⁰, —PR¹⁰ ₂,

—P(═W)R¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂,

aryl and heterocyclyl,

of which the two mentioned last are optionally substituted by one or more radicals from the group

 (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl,

 (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiRR¹⁰ ₃,

 —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —SOR¹⁰,

 —SO₂R¹⁰, nitro, cyano and hydroxyl,

aryl,

which is optionally substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl,

where these six abovementioned radicals are optionally substituted by one or more radicals from the group

 halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰,

 —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and

 —SO₂R¹⁰,

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰,

—C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰,

—OC(═W)OR¹⁰, —NR C(═W)R¹⁰, —N[C(═W)R¹⁰]₂,

—NR¹⁰C(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —PR¹⁰ ₃,

—SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂ and —PW₃R¹⁰ ₂,

pyridyl,

which is optionally substituted by one or more radicals from the group

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl,

where the six abovementioned radicals are optionally substituted by one or more radicals from the group

 cyano, nitro, halogen, —C(═W)R¹⁰, —C(═W)OR¹⁰,

 —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and

 —SO₂R¹⁰,

halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰,

—C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰, and —SO₂R¹⁰,

—C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰,

—C(═W)NR¹⁰ ₂ or halogen;

R⁴ and R⁵ together form a 4- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹;

R⁶ and R⁵ together form one of the groups ═O, ═S or ═N—R⁹;

R⁶ and R⁷ together form a 5- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹;

R⁶ and R⁷ together form one of the groups ═O, ═S or ═N—R⁹;

R⁸ is hydrogen,

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl,

where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl,

(C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkylthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio,

(C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkerlylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfinyl,

(C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl,

(C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalkylsulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfonyl, (C₃-C₁₈)-cycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfonyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl,

(C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino,

(C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylarnino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy,

arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy,

aryloxycarbonyl, aryl-(C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(C₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,

of which the nineteen last-mentioned radicals are optionally substituted in their cyclic moiety by one or more substituents from the group

 halogen, cyano, nitro, amino, hydroxyl, thio,

 (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino,

 formyl and (C₁-C₄)-alkanoyl,

aryl, which is optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, ((C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₃-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino and (C₄-C₈)-halocycloalkenylamino,

—C(═W)R¹¹, OR¹¹ or NR¹¹ ₂;

R⁹ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl,

where the nine last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆) alkynyloxy and (C₁-C₆)-haloalkyloxy;

R¹⁰ is hydrogen,

(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl,

where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl,

(C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio,

(C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylthio,

(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl,

(C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl₁ (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloa lkeny isulfiny l, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfinyl,

(C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl,

(C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfonyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfonyl,

(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkyriyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfonyl,

(C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino,

(C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy,

arylthio, arylamino, aryl-(C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio,

aryl-(C₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl,

where the cyclic moiety of the fourteen last-mentioned radicals is optionally substituted by one or more radicals from the group

 halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₃-C₈)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio,

(C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl and

(C₁-C₄)-alkanoyl,

aryl, 5- or 6-membered heteroaromatic,

where the two last-mentioned radicals are optionally substituted by one or more radicals from the group

halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkanoyloxy,

(C₁-C₆)-mono- or dihaloalkylcarbarnoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio,

(C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio,

(C₃-C₈)-halocycloalkthio, (C₄-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenlylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino,

(C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkylamino and (C₄-C₈)-halocycloalkenylamino;

R¹¹ is (C₁-C₁₀)-alkyl, haloalkyl, aryl,

which is optionally substituted by one or more radicals from the group

halogen, cyano, nitro, (C₁-C₄)-alkoxy, (C₁-C₄)-alkyl, amino, (C₁-C₄)-monoalkylamino and (C₁-C₄)-dialkylamino,

NR¹⁰ ₂, OR¹⁰ or SR¹⁰.

The numbers in brackets are the reference numbers from The Pesticide Manual, 11th edition, British Crop Protection Council, Farnham 1997.

The method according to the invention makes it possible to reduce the application rate of crop protection agents which act synergistically with the transgenic plants, and also to increase and widen the efficacy of the transgenic plants, and therefore offers economical and ecological advantages.

The advantages of the method are, on the one hand, synergisms with the Bacillus thuringiensis toxins (Bt toxins) produced in the transgenic plant and, on the other hand, for example, a reduced number of applications or a reduction of the application rates to in some instances sublethal dosages (compared to the conventional application of the individual insecticides) and an associated considerably reduced environmental burden.

In particular combinations of the abovementioned active compounds show, together with the endogenously produced Bt toxins (i.e. produced within the transgenic plants) a distinct synergistic effect on a large number of harmful organisms to be controlled.

The invention also provides the use of compounds from the abovementioned groups a-f for controlling harmful organisms in genetically modified cotton plants which contain a gene derived from Bacillus thuringiensis which encodes and expresses an insecticidally active protein.

For the purpose of the invention, the term “insecticidally active” includes insecticidal, nematicidal, ovicidal action, and a repellent, behavior-modifying and sterilent action.

Preferred insecticidally active compounds are the abovementioned groups (a) to (e), in particular the organophosphorus compounds, pyrethroids, carbamates, endosulfan, fipronil, abamectin, piperonyl butoxide, XDE-105 and Bacillus thuringiensis.

Particular preference is given to triazaphos, endosulfan, deltamethrin, fipronil, abamectin, piperonyl butoxide and Bacillus thuringiensis.

Preference is also given to mixtures of two or more, preferably two or three, particularly preferably two, of the insecticidally active compounds. Particular preference is given to mixtures of the abovementioned organophosphorus compounds with the abovementioned pyrethroids, for example of triazaphos with deltamethrin.

Likewise, particular preference is given to the mixtures listed below: deltamethrin and piperonyl butoxide, deltamethrin and fibronil, deltamethrin and endosulfan, deltamethrin and XDE-105, deltamethrin and chlorphenapyr, deltamethrin and Bacillus thuringiensis, endosulfan and amitraz, endosulfan and Bacillus thuringiensis, cyfluthrin and chlorpyriphos.

Likewise, preference is given to the 4-haloalkyl-3-heterocyclylpyridines and 4-haloalkyl-5-heterocyclylpyrimidines of group (f).

For these compounds:

The term “halogen” includes fluorine, chlorine, bromine and iodine.

The term “(C₁-C₄)-alkyl” is to be understood as a straight-chain or branched hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, such as, for example, the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical. Correspondingly, alkyl radicals having a greater range of carbon atoms are to be understood as straight-chain or branched saturated hydrocarbon radicals which contain a number of carbon atoms which corresponds to the range stated. Thus, the term “(C₁-C₆)-alkyl” includes the abovementioned alkyl radicals, and, for example, the pentyl, 2-methylbutyl, 1,1-dimethylpropyl, hexyl radical. The term “(C₁-C₁₀)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the nonyl, 1-decyl or 2-decyl radical and the term “(C₁-C₂₀)-alkyl” is to be understood as the abovementioned alkyl radicals, and, for example, the undecyl, dodecyl, pentadecyl or eicosyl radical.

“(C₁-C₄)-Haloalkyl” is to be understood as an alkyl group mentioned under the term “(C₁-C₄)-alkyl” in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, preferably by fluorine or chlorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl and the 1,1,2,2-tetrafluoroethyl group.

“(C₁-C₄)-Alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term “(el -C₄)-alkyl”. Alkoxy groups embracing a greater range of carbon atoms are to be understood correspondingly.

The terms “alkenyl” and “alkynyl” having a prefix stating the range of carbon atoms denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms corresponding to the range stated which comprises at least one multiple bond which may be in any position of the unsaturated radical in question. “(C₂-C₄)-Alkenyl” is thus, for example, the vinyl, allyl, 2-methyl-2-propene or 2-butenyl group; “(C₂-C₆)-alkenyl” denotes the abovementioned radicals and, for example, the pentenyl, 2-methylpentenyl or the hexenyl group. The term “(C₂-C₂₀)-alkenyl” is to be understood as the abovementioned radicals and, for example, the 2-decenyl or the 2-eicosenyl group. “(C₂-C₄)-Alkynyl” is, for example, the ethynyl, propargyl, 2-methyl-2-propyne or 2-butynyl group. “(C₂-C₆)-Alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-pentynyl- or the 2-hexynyl group and “(C₂-C₂₀)-alkynyl” is to be understood as the abovementioned radicals and, for example, the 2-octynyl or the 2-decynyl group.

“(C₃-C₈)-Cycloalkyl” denotes monocyclic alkyl radicals, such as the cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical and bicyclic alkyl radicals, such as the norbornyl radical.

The term “(C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl” is to be understood as, for example, the cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl and cyclohexylbutyl radical, and the term “(C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl is to be understood as, for example, the 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyclohexyl, 3-hexylcyclobutyl and 4-tert-butyl-cyclohexyl radical.

“(C₁-C₄)-Alkoxy-(C₁-C₆)-alkyloxy” is an alkoxy group as defined above which is substituted by a further alkoxy group, such as, for example, 1-ethoxyethoxy.

“(C₃-C₈)-Cycloalkoxy” or “(C₃-C₈)-cycloalkylthio” is to be understood as one of the abovementioned (C₃-C₈)-cycloalkyl radicals which is linked via an oxygen or sulfur atom.

“(C₃-C₈)-Cycloalkyl-(C₁-C₆)-alkoxy” is, for example, the cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylethoxy or the cyclohexylbutoxy group;

The term “(C₁-C₄)-alkyl-(C₃-C₈)-cycloalkoxy” is, for example, the methylcyclopropyloxy, methylcyclobutyloxy or the butylcyclohexyloxy group.

“(C₁-C₆)-Alkylthio” is an alkylthio group whose hydrocarbon radical has the meaning given under the term “(C₁-C₆)-alkyl”.

Correspondingly, “(C₁-C₆)-alkylsulfinyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfinyl group and

“(C₁-C₆)-alkylsulfonyl” is, for example, the methyl-, ethyl-, propyl-, isopropyl-, butyl-, isobutyl-, sec-butyl- or tert-butylsulfonyl group.

“(C₁-C₆)-Alkylamino” is a nitrogen atom which is substituted by one or two identical or different alkyl radicals of the above definition.

The term “(C₁-C₆)-mono- or dialkylcarbamoyl” is a carbamoyl group having one or two hydrocarbon radicals which have the meaning given under the term “(C₁-C₆-alkyl)” and which, in the case of two hydrocarbon radicals, may be identical or different.

Correspondingly, “(C₁-C₆)-dihaloalkylcarbamoyl” is a carbamoyl group which carries two (C₁-C₆)-haloalkyl radicals in accordance with the above definition or one (C₁-C₆)-haloalkyl radical and one (C₁-C₆)-alkyl radical in accordance with the above definition.

“(C₁-C₆)-Alkanoyl” is, for example, the acetyl, propionyl, butyryl or 2-methylbutyryl group.

The term “aryl” is to be understood as an isocyclic aromatic radical preferably having 6 to 14, in particular 6 to 12, carbon atoms, such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl. “Aroyl” is thus an aryl radical as defined above which is attached via a carbonyl group, such as, for example, the benzoyl group.

The term “heterocyclyl” denotes a cyclic radical which may be fully saturated, partially unsaturated or fully unsaturated and which may be interrupted by at least one or more identical atoms from the group nitrogen, sulfur or oxygen, oxygen atoms, however, not being directly adjacent to one another and at least one carbon atom being present in the ring, such as, for example, a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine 4H-quinolizine; piperidine, pyrrolidine, oxazoline, tetrahydrofuran, tetrahydropyran, isoxazolidine or thiazolidine radical. The term “heteroaromatic” thus embraces, from among the meanings mentioned above under “heterocyclyl”, in each case the fully unsaturated aromatic heterocyclic compounds.

“Aryl-(C₁-C₄)-alkoxy” is an aryl radical which is attached via a (C₁-C₄)-alkoxy group, for example the benzyloxy, phenylethoxy, phenylbutoxy or naphthylmethoxy radical.

“Arylthio” is an aryl radical attached via a sulfur atom, for example the Ephenylthio or the 1- or 2-naphthylthio radical. Correspondingly, “aryloxy” is, for example, the phenoxy or 1- or 2-naphthyloxy radical.

“Aryl-(C₁-C₄)-alkylthio” is an aryl radical which is attached via an alkylthio radical, for example the benzylthio, naphthylmethylthio or the iphenylethylthio radical.

The term “(C₁-C₆)-trialkylsilyl” denotes a silicon atom which carries three identical or different alkyl radicals in accordance with the above definition. Correspondingly “aryl-(C₁-C₆)-dialkylsilyl” is a silicon atom which carries one aryl radical and two identical or different radicals in accordance with the above defition, “diaryl-(C₁-C₆)-alkylsilyl” is a silicon atom which carries one alkyl radical and two identical or different aryl radicals in accordance with the above definition, and “triarylsilyl” is a silicon atom which carries three identical or different aryl radicals in accordance with the above definition.

In cases where two or more radicals R¹⁰ are present in a substituent, such as, for example, in —C(═W)NR¹⁰ ₂. these radicals may be identical or different.

Y in the formula (I) is preferably CF₃. Furthermore, X is preferably the group CH. Likewise, preference is given to compounds in which:

X₁=0 and X²=N and X³=CR¹. Likewise, preference is given to compounds where m=0.

Particular preference is given to compounds of the formula (I) from the group (f) in which the symbols Y, X, X, X¹, X², X³ have the preferred meanings given above, in particular to compounds in which m likewise has the preferred meaning.

Preference is given to those compounds from the group (D with the formula I in which

Y is C₁-C₆-alkyl which is mono- or polysubstituted by chlorine and/or fluorine;

m is zero;

Q is a 5-membered heterocyclic group

 in which

a) X²=NR^(a) and X³=CR^(b)R¹ or

b) X²=CR^(a)R²and X³=CR^(b)R³ or

c) X²=CR⁴R⁵ and X³=CR⁶R⁷;

R^(a) and R^(b) together are a bond;

R¹, R², R³, R⁴ and R⁶ are each independently of one another hydrogen, halogen, C₁-C₁₂-alkyl, C₃-C₈-cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A1 consisting of C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino, C₁-C₆-alkylcarbonylamino, C₁-C₆-alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group Al are each optionally mono- or polysubstituted by identical or different radicals from a group B1 consisting of halogen, cyano, C₁-C₃-alkoxy and phenyl which is optionally mono- or polysubstituted by one or more halogen atoms and where the three last-mentioned radicals of group A1 are each optionally mono- or polysubstituted by identical or different radicals from a group B2 consisting of halogen, cyano, nitro, C₁-C₃-alkyl and C₁-C₃-alkoxy, or are C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from group B1, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R⁵ and R⁷ are each independently of one another hydrogen, halogen, C₁-C₁₂-alkyl, C₃-C₈-cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, where the four last-mentioned hydrocarbon radicals are optionally mono- or polysubstituted by identical or different radicals from a group A2 consisting of C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylamino, C₁-C₆-alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, halogen, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A2 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are C₁-C₆-alkylcarbonyl, C₁-C₆-alkylaminocarbonyl, C₁-C₆-alkoxycarbonyl, phenyl, pyridyl, furyl, thienyl, pyrryl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from the group B1, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R¹⁰ is hydrogen, benzyl, C₁-C₆-alkyl, C₁-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, C₁-C₆-alkylcarbonyl or C₁-C₆-alkylsulfonyl, where the eight last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.

Particular preference is given to compounds from the group (f) with the formula I in which

Y is trifluoromethyl;

R¹, R², R³ R⁴ and R⁶ are each independently of one another halogen, C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A3 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, C₁-C₄-alkylsulfonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eleven first-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A3 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R⁵ and R⁷ are each independently of one another halogen, C₁-C₁₂-alkyl, C₂-C₁₂-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A4 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, phenyl, furyl, pyrryl, thienyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the ten first-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A4 are each optionally mono- or polysubstituted by identical or different radicals from the group B2, or are OR¹⁰, SR¹⁰ or N(R¹⁰)₂;

R¹⁰ is hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, phenyl, C₁-C₄-alkylcarbonyl or C₁-C₄-alkylsulfonyl, where the six last-mentioned radicals are optionally mono- or polysubstituted by identical or different halogen atoms.

Very particular preference is given to compounds from the group (f) with the formula I in which

R¹, R², R³, R⁴ and R⁶ are each independently of one another C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A5 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, C₁-C₄-alkylsulfonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the eight first-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A5 are each optionally mono- or polysubstituted by identical or different radicals from the group B2;

R⁵ and R⁷ are each independently of one another C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, where the two last-mentioned radicals are optionally mono- or polysubstituted by identical or different radicals from a group A6 consisting of C₁-C₄-alkylcarbonyl, C₁-C₄-alkylaminocarbonyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylamino, C₁-C₄-alkylcarbonylamino, phenyl, fluorine, chlorine, bromine, cyano, phenyloxy, phenylthio and phenylamino, where the seven first-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B1 and the three last-mentioned radicals of group A6 are each optionally mono- or polysubstituted by identical or different radicals from the group B2.

Particularly preferred compounds from the group (f) with the formula (I) are listed in the following Tables 1 to 5:

TABLE 1

No. X Y m W R¹ m.p. [° C.]  1 N CCl₃ 0 O CH₃  2 N CCl₃ 0 O CH₂CH₃  3 N CCl₃ 0 O COOCH₂CH₃  4 CH CCl₃ 0 O CH₃  5 CH CCl₃ 0 O COOCH₂CH₃  6 N (CF₂)₃CHF₂ 0 O CH₃  7 N (CF₂)₃CHF₂ 0 O COOCH₂CH₃  8 CH (CF₂)₃CHF₂ 0 O CH₃  9 CH (CF₂)₃CHF₂ 0 O COOCH₂CH₃  10 N (CF₂)₃CHF₂ 0 S CH₂COOC(CH₃)₃  11 N (CF₂)₃CHF₂ 0 S CH₂CONHCH₃  12 CH (CF₂)₃CHF₂ 0 S (CH₂)₂CH₃  13 CH (CF₂)₃CHF₂ 0 S COOCH₂CH₃  14 N (CF₂)₂CHF₂ 0 O CH₂CH₃  15 N (CF₂)₂CHF₂ 0 O COOCH₂CH₃  16 N (CF₂)₂CHF₂ 0 O OH  17 N (CF₂)₂CHF₂ 0 O OCH₃  18 CH (CF₂)₂CHF₂ 0 O CH₃  19 CH (CF₂)₂CHF₂ 0 O COOCH₂CH₃  20 CH (CF₂)₂CHF₂ 0 O OH  21 CH (CF₂)₂CHF₂ 0 O NHCH₃  22 N CF₂CF₃ 0 O CH₃  23 N CF₂CF₃ 0 O CH₂CH₃  24 N CF₂CF₃ 0 O (CH₂)₂CH₃  25 N CF₂CF₃ 0 O CH(CH₃)₂  26 N CF₂CF₃ 0 O Cyclo-C₆H₁₁  27 N CF₂CF₃ 0 O CH₂C═CH₂  28 N CF₂CF₃ 0 O CH₂C≡CH  29 N CF₂CF₃ 0 O CH₂CH₂C≡CH  30 N CF₂CF₃ 0 O CH₂C≡CCH₂CH₃  31 N CF₂CF₃ 0 O (CH₂)₄C≡CH  32 N CF₂CF₃ 0 O CHFCF₃  33 N CF₂CF₃ 0 O COOCH₂CH₃  34 N CF₂CF₃ 0 O CH₂COOC(CH₃)₃  35 N CF₂CF₃ 0 O CH₂CONHCH₃  36 N CF₂CF₃ 0 O NH₂  37 N CF₂CF₃ 0 O NHCH₂CH₃  38 CH CF₂CF₃ 0 O CH₃  39 CH CF₂CF₃ 0 O CH₂CH₃  40 CH CF₂CF₃ 0 O (CH₂)₂CH₃  41 CH CF₂CF₃ 0 O CH(CH₃)₂  42 CH CF₂CF₃ 0 O Cyclo-C₆H₁₁  43 CH CF₂CF₃ 0 O CH₂C═CH₂  44 CH CF₂CF₃ 0 O CH₂COOC(CH₃)₃  45 CH CF₂CF₃ 0 O NH₂  46 CH CF₂CF₃ 0 O NHCOCH₃  47 CH CF₂CF₃ 0 O NHCOCH₂CH₃  48 N CF₂CF₃ 0 S CH₃  49 N CF₂CF₃ 0 S CH₂CH₃  50 N CF₂CF₃ 0 S (CH₂)₂CH₃  51 N CF₂Cl 0 O CH₃  52 N CF₂Cl 0 O CH₂CH₃  53 N CF₂Cl 0 O (CH₂)₂CH₃  54 N CF₂Cl 0 O CH(CH₃)₂  55 N CF₂Cl 0 O CH₂COOC(CH₃)₃  56 N CF₂Cl 0 O CH₂CONHCH₃  57 N CF₂Cl 0 O OH  58 N CF₂Cl 0 O OCH₃  59 N CF₂Cl 0 O OCH₂CH₃  60 N CF₂Cl 0 O NHCH₃  61 CH CF₂Cl 0 O CH₃  62 CH CF₂Cl 0 O CH₂CH₃  63 CH CF₂Cl 0 O (CH₂)₂CH₃  64 CH CF₂Cl 0 O CH(CH₃)₂  65 CH CF₂Cl 0 O CH₂COOC(CH₃)₃  66 CH CF₂Cl 0 O CH₂CONHCH₃  67 CH CF₂Cl 0 O OH  68 CH CF₂Cl 0 O OCH₃  69 CH CF₂Cl 0 O OCH₂CH₃  70 CH CF₂Cl 0 O NHCH₃  71 CH CF₂Cl 0 O Cyclo-C₆H₁₁  72 CH CF₂Cl 0 O CH₂C═CH₂  73 CH CF₂Cl 0 O COOCH₂CH₃  74 CH CF₂Cl 0 O CH₂COOC(CH₃)₃  75 CH CF₂Cl 0 O CH₂CONHCH₃  76 CH CF₂Cl 0 O OCH₃  77 CH CF₂Cl 0 O NHCH₃  78 CH CF₃ 0 O CH₃ oil  79 CH CF₃ 0 O CH₂CH₃ oil  80 CH CF₃ 0 O (CH₂)₂CH₃ oil  81 CH CF₃ 0 O CH(CH₃)₂ oil  82 CH CF₃ 0 O Cyclo-C₃H₅ oil  83 CH CF₃ 0 O (CH₂)₃CH₃ oil  84 CH CF₃ 0 O CH(CH₃)CH₂CH₃ oil  85 CH CF₃ 0 O CH₂CH(CH₃)₂ oil  86 CH CF₃ 0 O C(CH₃)₃ oil  87 CH CF₃ 0 O Cyclo-C₄H₇  88 CH CF₃ 0 O (CH₂)₄CH₃ oil  89 CH CF₃ 0 O CH(CH₃)(CH₂)₂CH₃  90 CH CF₃ 0 O (CH₂)₂CH(CH₃)₂  91 CH CF₃ 0 O CH₂C(CH₃)₃  92 CH CF₃ 0 O Cyclo-C₅H₉ oil  93 CH CF₃ 0 O (CH₂)₅CH₃  94 CH CF₃ 0 O C(CH₂CH₃)₂CH₃  95 CH CF₃ 0 O Cyclo-C₆H₁₁  96 CH CF₃ 0 O (CH₂)₆CH₃  97 CH CF₃ 0 O CH(CH₃)(CH₂)₄CH₃  98 CH CF₃ 0 O Cyclo-C₇H₁₃  99 CH CF₃ 0 O CH₂-cyclo-C₆H₁₁ 100 CH CF₃ 0 O 2-Norbornyl 101 CH CF₃ 0 O (CH₂)₇CH₃ 102 CH CF₃ 0 O CH(CH₂CH₃)(CH₂)₅CH₃ 103 CH CF₃ 0 O (CH₂)₈CH₃ 104 CH CF₃ 0 O (CH₂)₃-cyclo-C₆H₁₁ 105 CH CF₃ 0 O (CH₂)₉CH₃ 106 CH CF₃ 0 O 1-Adamantyl 107 CH CF₃ 0 O (CH₂)₁₀CH₃ 108 CH CF₃ 0 O (CH₂)₁₁CH₃ 109 CH CF₃ 0 O CH(CH₃)(CH₂)₉CH₃ 110 CH CF₃ 0 O (CH₂)₁₂CH₃ 111 CH CF₃ 0 O (CH₂)₁₃CH₃ 112 CH CF₃ 0 O (CH₂)₁₄CH₃ 113 CH CF₃ 0 O (CH₂)₁₅CH₃ 114 CH CF₃ 0 O (CH₂)₁₇CH₃ 115 CH CF₃ 0 O (CH₂)₁₉CH₃ 116 CH CF₃ 0 O CHO 117 CH CF₃ 0 O CH═CH₂ oil 118 CH CF₃ 0 O CH₂C═C(CH₃)₂ 119 CH CF₃ 0 O CH₂CH₂C═CH₂ 120 CH CF₃ 0 O CH₂C═CH₂ 121 CH CF₃ 0 O C(CH₃)═CH₂ 122 CH CF₃ 0 O (E)-CH₂CH═CHCH₂CH₃ 123 CH CF₃ 0 O (Z)-CH₂CH═CHCH₂CH₃ 124 CH CF₃ 0 O (CH₂)₅C═CH₂ 125 CH CF₃ 0 O C(═CHCH₃)CH₃ 62-64 126 CH CF₃ 0 O Geranyl 127 CH CF₃ 0 O 3-Menthyl 128 CH CF₃ 0 O C≡CH 129 CH CF₃ 0 O CH₂C≡CH 130 CH CF₃ 0 O CH₂CH₂C≡CH 131 CH CF₃ 0 O CH₂CH₂C≡CH 132 CH CF₃ 0 O (CH₂)₄C≡CH 133 CH CF₃ 0 O CHFCF₃ oil 134 CH CF₃ 0 O COOCH₂CH₃ oil 135 CH CF₃ 0 O CH₂CH₂OH oil 136 CH CF₃ 0 O CH₂CH₂OCH₃ oil 137 CH CF₃ 0 O CH₂COOC(CH₃)₃ oil 138 CH CF₃ 0 O CH₂SC₆H₅ oil 139 CH CF₃ 0 O CH₂CONHCH₃ 109-111 140 CH CF₃ 0 O CH₂CH(OH)CH₂OH 141 CH CF₃ 0 O CH₂COCH₃ 142 CH CF₃ 0 O COCH₃ 143 CH CF₃ 0 O CH₂OC₆H₅ 144 CH CF₃ 0 O COC₆H₅ 145 CH CF₃ 0 O CO(4-Cl)—C₆H₄ 146 CH CF₃ 0 O CF₂CH₃ 147 CH CF₃ 0 O CH₂CN 148 CH CF₃ 0 O CH₂CH₂CN 149 CH CF₃ 0 O CH₂CH(—O—)CH₂ 150 CH CF₃ 0 O CH₂(4-OCH₃)C₆H₅ 151 CH CF₃ 0 O CH₂-cyclo-(4-Oxo)—C₆H₈ 152 CH CF₃ 0 O CH₂CH(OH)CH₂SC₆H₅ 153 CH CF₃ 0 O CH₂CH₂Si(CH₃)₃ 154 CH CF₃ 0 O CH═CF₂ 155 CH CF₃ 0 O CCl═CHCl 156 CH CF₃ 0 O 2-Pyridyl  99-101 157 CH CF₃ 0 O 2-Furyl 158 CH CF₃ 0 O 2-Thienyl 106-108 159 CH CF₃ 0 O CH₂C≡CCH₂CH₂OTHP 160 CH CF₃ 0 O CH₂CH₂Cl oil 161 CH CF₃ 0 O Si(CH₃)₃ 162 CH CF₃ 0 O OC₆H₅ 163 CH CF₃ 0 O OH 164 CH CF₃ 0 O OCH₃ 165 CH CF₃ 0 O OCH₂CH₃ 166 CH CF₃ 0 O OCHF₂ 167 CH CF₃ 0 O OCH₂C₆H₅ 168 CH CF₃ 0 O CH₂SCH₃ 48-49 169 CH CF₃ 0 O SC₆H₅ 170 CH CF₃ 0 O SeC₆H₅ 171 CH CF₃ 0 O NH₂ 116-118 172 CH CF₃ 0 O NHCH₃ 173 CH CF₃ 0 O NHCH₂CH₃ 174 CH CF₃ 0 O N(CH₂CH₃)₂ 175 CH CF₃ 0 O CONHCH₂C═CH₂ 105-107 176 CH CF₃ 0 O Cl 177 CH CF₃ 0 O Br 178 CH CF₃ 0 O CONH₂ 206-208 179 CH CF₃ 0 O NHCOCH₃ 129-131 180 CH CF₃ 0 O NHCOCH₂CH₃ 181 CH CF₃ 0 O OSO₂CH₃ 182 CH CF₃ 0 O SOCH₂(4-Br)—C₆H₄ 183 CH CF₃ 0 O N(CH₃)COOCH₂C₆H₅ 184 CH CF₃ 0 O NHNH₂ 185 CH CF₃ 0 O NHN(CH₃)₂ 186 N CF₃ 0 O CH₃ 187 N CF₃ 0 O CH₂CH₃ oil 188 N CF₃ 0 O (CH₂)₂CH₃ oil 189 N CF₃ 0 O CH(CH₃)₂ oil 190 N CF₃ 0 O (CH₂)₃CH₃ oil 191 N CF₃ 0 O CH₂CH(CH₃)₂ oil 192 N CF₃ 0 O C(CH₃)₃ 193 N CF₃ 0 O (CH₂)₄CH₃ oil 194 N CF₃ 0 O CH(CH₃)(CH₂)₂CH₃ 195 N CF₃ 0 O CH₂C(CH₃)₃ 196 N CF₃ 0 O Cyclo-C₅H₉ 197 N CF₃ 0 O (CH₂)₅CH₃ 198 N CF₃ 0 O Cyclo-C₆H₁₁ 199 N CF₃ 0 O CH(CH₃)(CH₂)₄CH₃ 200 N CF₃ 0 O CH₂-cyclo-C₆H₁₁ 201 N CF₃ 0 O (CH₂)₇CH₃ 202 N CF₃ 0 O (CH₂)₈CH₃ 203 N CF₃ 0 O (CH₂)₉CH₃ 204 N CF₃ 0 O CH(CH₃)(CH₂)₉CH₃ 205 N CF₃ 0 O (CH₂)₁₅CH₃ 206 N CF₃ 0 O (CH₂)₁₇CH₃ 207 N CF₃ 0 O (CH₂)₁₉CH₃ 208 N CF₃ 0 O CH₂CH═C(CH₃)₂ 209 N CF₃ 0 O CH₂CH₂CH═CH₂ 210 N CF₃ 0 O CH₂CH═CH₂ 211 N CF₃ 0 O (Z)-CH₂CH═CHCH₂CH₃ 212 N CF₃ 0 O (CH₂)₅CH═CH₂ 213 N CF₃ 0 O CH₂C≡CH 214 N CF₃ 0 O CH₂C≡CCH₂CH₃ 215 N CF₃ 0 O CHFCF₃ 216 N CF₃ 0 O COOCH₂CH₃ 217 N CF₃ 0 O CH₂CH₂OH 218 N CF₃ 0 O CH₂CH₂OCH₃ 219 N CF₃ 0 O CH₂COOC(CH₃)₃ 220 N CF₃ 0 O CH₂SC₆H₅ 221 N CF₃ 0 O CH₂CONHCH₃ 222 N CF₃ 0 O CH₂CH(OH)CH₂OH 223 N CF₃ 0 O CHO 224 N CF₃ 0 O COCH₃ 225 N CF₃ 0 O CH₂OC₆H₅ 226 N CF₃ 0 O COC₆H₅ 227 N CF₃ 0 O CF₂CH₃ 228 N CF₃ 0 O CH₂CN 229 N CF₃ 0 O CH₂CH₂CN 230 N CF₃ 0 O CH═CF₂ 231 N CF₃ 0 O 2-Furyl 232 N CF₃ 0 O CH₂C≡C—I 233 N CF₃ 0 O OH 234 N CF₃ 0 O OCH₃ 235 N CF₃ 0 O OCH₂CH₃ 236 N CF₃ 0 O OCHF₂ 237 N CF₃ 0 O OCH₂C₆H₅ 238 N CF₃ 0 O SC₆H₅ 239 N CF₃ 0 O NH₂ 240 N CF₃ 0 O NHCH₃ 241 N CF₃ 0 O NHCH₂CH₃ 242 N CF₃ 0 O N(CH₂CH₃)₂ 243 N CF₃ 0 O N(CH₂CN)₂ 244 N CF₃ 0 O N(CH₃)₂ 245 N CF₃ 0 O NHCOCH₃ 246 N CF₃ 0 O NHCOCH₂CH₃ 247 N CF₃ 0 O OSO₂CH₃ 248 N CF₃ 0 O NHNH₂ 249 CH CF₃ 0 S CH₃ 250 CH CF₃ 0 S CH₂CH₃ 251 CH CF₃ 0 S (CH₂)₂CH₃ 252 CH CF₃ 0 S CHO 253 CH CF₃ 0 S CHFCF₃ 254 CH CF₃ 0 S CH₂C≡CH 255 CH CF₃ 0 S COOCH₂CH₃ 256 CH CF₃ 0 S CH₂COOC(CH₃)₃ 257 CH CF₃ 0 S CH₂CN 258 CH CF₃ 0 S SeC₆H₅ 259 N CF₃ 0 S CH₃ 260 N CF₃ 0 S CH₂CH₃ 261 N CF₃ 0 S (CH₂)₂CH₃ 262 N CF₃ 0 S CHFCF₃ 263 N CF₃ 0 S CH₂CH₂OH 264 N CF₃ 0 S CH₂COOC(CH₃)₃ 265 CH CH₂CH₂Cl 0 O CH₃ 266 CH CH₂CH₂Cl 0 O CH₂CH₃ 267 CH CH₂CH₂Cl 0 O (CH₂)₂CH₃ 268 CH CH₂CH₂Cl 0 O CH(CH₃)₂ 269 CH CH₂CH₂Cl 0 O CH₂SC₆H₅ 270 CH CH₂CH₂Cl 0 O CH₂CONHCH₃ 271 CH CH₂CH₂Cl 0 O NH₂ 272 CH CH₂CH₂Cl 0 O NHCH₂CH₃ 273 N CH₂CH₂Cl 0 O CH₂CH₃ 274 N CH₂CH₂Cl 0 O NH₂ 275 N CH₂Cl 0 O CH₃ 276 CH CH₂Cl 0 O CH₃ 277 CH CHF₂ 0 O CH₃ 278 CH CHF₂ 0 O CH₂CH₃ 279 CH CHF₂ 0 O (CH₂)₂CH₃ 280 CH CHF₂ 0 O CH₂CH═CH₂ 281 CH CHF₂ 0 O C(CH₃)═CH₂ 282 CH CHF₂ 0 O COOCH₂CH₃ 283 CH CHF₂ 0 O CH₂CONHCH₃ 284 CH CHF₂ 0 O CF₂CH₃ 285 CH CHF₂ 0 O CHO 286 CH CHF₂ 0 O NH₂ 287 CH CHF₂ 0 O Cl 288 CH CHF₂ 0 O NHCOCH₃ 289 CH CHF₂ 0 O NHNH₂ 290 N CHF₂ 0 O CH₃ 291 N CHF₂ 0 O CH₂CH₃ 292 N CHF₂ 0 O CH(CH₃)(CH₂)₄CH₃ 293 N CHF₂ 0 O CH₂CH═CH₂ 294 N CHF₂ 0 O COOCH₂CH₃ 295 N CHF₂ 0 O NH₂ 296 CH CF₃ 1 O CH₃ 297 CH CF₃ 1 O COOCH₂CH₃ 298 CH CF₃ 1 O CH₂COOC(CH₃)₃ 299 CH CF₃ 1 O CHFCF₃ 300 N CF₃ 0 O CH₂NHSO₂CH₃ 301 N CF₃ 0 O (CH₂)₂NHSO₂CH₃ 302 N CF₃ 0 O CH₂NHSO₂CH₂CH₃ 303 N CF₃ 0 O CH₂NHSO₂CH₂C₆H₅ 304 CH CF₃ 0 O (CH₂)₄NHSO₂CF₃ 305 CH CF₃ 0 O (CH₂)₂S(CH₂)₂CH₃ 306 CH CF₃ 0 O (CH₂)₄S(CH₂)₄OCH₃ 307 CH CF₃ 0 S (CH₂)₂S(CH₂)₂CN 308 CH CF₃ 0 S CH₂NHSO₂CH₂CH₃ 309 CH CF₃ 0 S CH₂NHSO₂CH₂C₆H₅ 310 CH CF₃ 0 S (CH₂)₂NHSO₂CH₃ 311 CH CF₃ 0 S CH₂NHSO₂CH₃ 312 CH CF₃ 0 S CH(CH₃)CH₂NHC₆H₅ 313 CH CF₃ 0 S (CH₂)₂S(2-F)—C₆H₄ 314 CH CF₃ 0 S (CH₂)₆NHCH₂)₆OCH₃ 315 CH CF₃ 0 S (CH₂)₂NH—(2-F)—C₆H₄ 316 CH CF₃ 0 S (CH₂)₃NHCH₂CN 317 CH CF₃ 0 S (CH₂)₂O(3-Cl)—C₆H₄ 318 CH CF₃ 0 S (CH₂)₆NHCH₂CF₃ 319 CH CF₃ 0 S (CH₂)₂O(3-CH₃)—C₆H₄ 320 CH CF₃ 0 O CH₂NHC₆H₅ 321 CH CF₃ 0 O (CH₂)₄S(2-Br)—C₆H₄ 322 CH CF₃ 0 O (CH₂)₆NH(CH₂)₂OCH₃ 323 CH CF₃ 0 O (CH₂)₂NH(CH₂)₄OCH₃ 324 CH CF₃ 0 O (CH₂)₃NH—(4-CN)—C₆H₄ 325 CH CF₃ 0 O (CH₂)₂O(3-CH₃)—C₆H₄ 326 CH CF₃ 0 O (CH₂)₄NHCH₂CF₃ 327 CH CF₃ 0 O (CH₂)₄NHCH₂CN 328 CH CF₃ 0 O (CH₂)₃O(4-OCH₃)—C₆H₄ 329 CH CF₃ 0 O CH₂SO₂-tert-C₄H₉ oil 330 CH CF₃ 0 O CH₂SO₂—(4-F)—C₆H₄ oil 331 CH CF₃ 0 O CH₂SO₂—C₆H₅ oil 332 CH CF₃ 0 O CH₂SOCH₃  63 333 CH CF₃ 0 O CH₂SO—C₆H₅ oil 334 CH CF₃ 0 O CH₂CONH(CH₂)₂CH₃ 80-82 335 CH CF₃ 0 O (4-OCF₃)—C₆H₄ 57-59 336 CH CF₃ 0 O CH₂OCH₃ oil 337 CH CF₃ 0 O

53-54 338 CH CF₃ 0 O

oil 339 CH CF₃ 0 O CH₂CH₂OCH₂CH₃ oil 340 CH CF₃ 0 O CH₂CH₂NC₆H₅ 80-83 341 CH CF₃ 0 O

80-81 342 CH CF₃ 0 O

110-111 343 CH CF₃ 0 O CH₂CH₂O(CO)—(4-Cl)—C₆H₄ 80-82 344 CH CF₃ 0 O CH₂—(4-OCH₃)—C₆H₄ 54-55 345 CH CF₃ 0 O CH₂—(3-Cl)—C₆H₄ 51-52 346 CH CF₃ 0 O CH₂-cyclo-C₃H₅ oil 347 CH CF₃ 0 O CH₂—(4-C₆H₅)—C₆H₄ oil 348 CH CF₃ 0 O

143-144 349 CH CF₃ 0 O CH₂CH₂O(CO)—(2,6-F₂)—C₆H₃ 57-58 350 CH CF₃ 0 O CH₂CH₂O(CO)—(4-NO₂)—C₆H₄ 80-81 351 CH CF₃ 0 O CH₂—(2,6-Cl₂)—C₆H₃ 91-92 352 CH CF₃ 0 O CH₂CH₂OSO₂CH₃ oil 353 CH CF₃ 0 O CH₂CH₂O(CO)-tert-C₄H₉ oil 354 CH CF₃ 0 O CH₂—(3-F)—C₆H₄ 50-51 355 CH CF₃ 0 O CH₂CONCH₂C≡CH 129-131 356 CH CF₃ 0 O CH₂CH₂O(CO)-cyclo-C₃H₇ oil 357 CH CF₃ 0 O CH₂CH₂O(CO)CH₃ oil 358 CH CF₃ 0 O CH₂—[2,4-(CH₃)₂]—C₆H₃ 85-86 359 CH CF₃ 0 O CH₂CONCH₂CH═CH₂ 210-212 360 CH CF₃ 0 O CH₂CON(CH₂CH₃)₂ oil 361 CH CF₃ 0 O CH₂CON(CH₂)₃CH₃ 77-79 362 CH CF₃ 0 O CH₂CONCH₂—(2-furyl) 139-141 363 CH CF₃ 0 O CH₂CONCH(CH₃)₂ 112-114 364 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₂)₄CH₃] 73-75 365 CH CF₃ 0 O CH₂CONCH₂CH₂C₆H₅ 120-122 366 CH CF₃ 0 O CH₂CONCH₂CH₂OCH₂CH₃  78 367 CH CF₃ 0 O CH₂CONCH₂CF₃ 176-178 368 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₂)₅CH₃] 85-86 369 CH CF₃ 0 O

oil 370 CH CF₃ 0 O

oil 371 CH CF₃ 0 O CH₂CH₂—(1-pyrryl) oil 372 CH CF₃ 0 O CH₂CH₂C₆H₅ oil 373 CH CF₃ 0 O CH₂Cl 53-54 374 CH CF₃ 0 O (CH₂)₃OH 38-39 375 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₂)₂]CH₃ 68-69 376 CH CF₃ 0 O CH₂CH(OCH₃)₂ oil 377 CH CF₃ 0 O CH₂CONCH₂C(CH₃)₃ oil 378 CH CF₃ 0 O CH₂CONC(CH₃)₂(CH₂CH₃) oil 379 CH CF₃ 0 O CH₂CONCH₂CH₂-cyclo-C₆H₁₁ 82-85 380 CH CF₃ 0 O CH₂CONCH(CH₃)(1-naphthyl) 142-146 381 CH CF₃ 0 O (CH₂)₃Cl oil 382 CH CF₃ 0 O CH₂CON-tert-C₄H₉ oil 383 CH CF₃ 0 O CH₂CON(iso-C₃H₇)₂ 70-72 384 CH CF₃ 0 O CH₂CON(CH₂)₇CH₃ 79-81 385 CH CF₃ 0 O CH₂CON-cyclo-C₆H₁₁ 119-121 386 CH CF₃ 0 O CH₂CONCH₂CH₂—(4-Cl)—C₆H₄ 120-121 387 CH CF₃ 0 O CH₂CONCH₂-(2-thienyl) 137-139 388 CH CF₃ 0 O

151-153 389 CH CF₃ 0 O CH₂CONHCH(CH₃)(CH₂CH₃) 87-89 390 CH CF₃ 0 O (CH₂)₃SCH₃ oil 391 CH CF₃ 0 O (CH₂)₃SOCH₃ oil 392 CH CF₃ 0 O CH₂CONC(CH₃)₂(C≡CH) 111-113 393 CH CF₃ 0 O CH₂CONCH(CH₃)CH₂CH₂CH(CH₃)₂ 72-74 394 CH CF₃ 0 O

oil 395 CH CF₃ 0 O CH₂CON-cyclo-C₅H₉ 110-112 396 CH CF₃ 0 O CH₂CON(CH₂)₄CH₃ 75-77 397 CH CF₃ 0 O

190-192 398 CH CF₃ 0 O CH₂CON(3-CF₃)C₆H₄ 136-138 399 CH CF₃ 0 O CH₂CON-cyclo-C₈H₁₇ 115-117 400 CH CF₃ 0 O

oil 401 CH CF₃ 0 O CH₂CON-Adamantyl oil 402 CH CF₃ 0 O CH₂CON(CH₂CH₂CH₃)₂ oil 403 CH CF₃ 0 O CH₂CONCH(CH₃)[(4-F)—C₆H₄] 111-113 404 CH CF₃ 0 O CH₂CONCH₂CH(CH₃)₂ 91-93 405 CH CF₃ 0 O

Oil 406 CH CF₃ 0 O CH₂CONCH₂CH₂OC₆H₅  99-101 407 CH CF₃ 0 O CH₂CH═NOCH₃ oil 408 CH CF₃ 0 O CH₂CONCH₂CH₂—[3,4-(OCH₃)₂]C₆H₃ 123-125 409 CH CF₃ 0 O CH₂CON—(2-Cl)C₆H₄ 138-140 410 CH CF₃ 0 O CH₂CON—(2-SCH₃)C₆H₄ 136-138 411 CH CF₃ 0 O

222-225 412 CH CF₃ 0 O

207-209 413 CH CF₃ 0 O CH₂CON—(3-Br)C₆H₄ 129-131 414 CH CF₃ 0 O CH₂CON—N—(2,4,6-Cl₃)C₆H₂ 153-155 415 CH CF₃ 0 O CH₂CON—(4-I)C₆H₄ 143-145 416 CH CF₃ 0 O CH₂CON—NCOCH₂(3-Thienyl) 185-187 417 CH CF₃ 0 O CH₂CH₂CHO oil 418 CH CF₃ 0 O CH₂CON(CH₃)[(CH₂)₃CH₃] oil 419 CH CF₃ 0 O CH₂CON—(3,5-Cl₂-2,4-F₂)C₆H 166-167 420 CH CF₃ 0 O CH₂CON—C₆H₅ 215-217 421 CH CF₃ 0 O CH₂CON(CH₃)(C₆H₁₁) oil 422 CH CF₃ 0 O CH₂CON(CH₂CH₃)(CH₂CH═CH₂) oil 423 CH CF₃ 0 O CH₂CON(CH₂CH₃)[CH(CH₃)₂] oil 424 CH CF₃ 0 O CH₂CONCH(CH₃)[(CH₃)₂] 108-110 425 CH CF₃ 0 O CH₂CON(CH₂CH₃)[CH₂C(═CH₂)(CH₃)] oil 426 CH CF₃ 0 O CH₂CONCH₂(4-tert-C₄H₉)C₆H₄ oil 427 CH CF₃ 0 O CH₂CONCH(CH₃)(tert-C₄H₉₎ oil 428 CH CF₃ 0 O CH₂CONCH(CH₃)[CH₂CH(CH₃)(CH₂CH₃)] oil 429 CH CF₃ 0 O CH₂CONCH₂COOCH₂CH₃ 103-105 430 CH CF₃ 0 O CH₂CON[(CH₂)₂CH₃](CH₂-cyclo-C₃H₇) oil 431 CH CF₃ 0 O CH₂CONCH(CH₃)CH₂CH₂CH(CH₃)₂ 80-82 432 CH CF₃ 0 O CH₂CONCH(CH₂CH₃)[CH₂CH(CH₃)₂] oil 433 CH CF₃ 0 O CH₂C═O—(1-Piperidinyl) oil 434 CH CF₃ 0 O

180-182 435 CH CF₃ 0 O CH₂CONCH₂C(═CH₂)(CH₃) 86-87 436 CH CF₃ 0 O CH₂CONCH[CH(CH₃)₂](COOCH₃) oil 437 CH CF₃ 0 O CH₂CONCH₂-cyclo-C₃H₇ oil 438 CH CF₃ 0 O CH₂CON(CH₂)₅OH oil 439 CH CF₃ 0 O CH₂CON(CH₃)(CH₂CO₂CH₃) oil 440 CH CF₃ 0 O CH₂CON(CH₃)(CH₂CN) oil 441 CH CF₃ 0 O CH₂CONCH[CH₂CH(CH₃)₂](CO₂CH₃) oil 442 CH CF₃ 0 O CH₂CON-(1-Piperidinyl) oil 443 CH CF₃ 0 O CH₂CONCH₂CH₂OCH₃ 97-99 444 CH CF₃ 0 O CH₂CH₂SC₆H₅ oil 445 CH CF₃ 0 O CH₂CH₂SCH₃ oil 446 CH CF₃ 0 O CH₂CH₂SCH₂C₆H₅ oil 447 CH CF₃ 0 O

oil 448 CH CF₃ 0 O CH₂CON—(2-OH)C₆H₄ 162-164 449 CH CF₃ 0 O CH₂CON—(3-OH)C₆H₄ oil 450 CH CF₃ 0 O CH₂CON—(2-CH₃)C₆H₄ 163-164 451 CH CF₃ 0 O CH₂CON—(3-NO₂)C₆H₄ 176-178 452 CH CF₃ 0 O CH₂CON—(3-OCF₂CHFCl)C₆H₄ 120-121 453 CH CF₃ 0 O CH₂CON—(3-CF₃-4-F)C₆H₃ 168-170 454 CH CF₃ 0 O CH₂CON—(2,4-Cl₂)C₆H₃ 120-122 455 CH CF₃ 0 O CH₂CON—(2-F,4.Cl)C₆H₃ 148-151 456 CH CF₃ 0 O CH₂CON—[2,4-(CH₃)₂]C₆H₃ 123-125 457 CH CF₃ 0 O CH₂CON—[2,3-(CH₃)₂]C₆H₃ waxy 458 CH CF₃ 0 O

waxy 459 CH CF₃ 0 O CH₂CON—(2-CH₃-3-Cl)C₆H₃ 160-162 460 CH CF₃ 0 O CH₂CON(CH₂CH₃)(C₆H₅) oil 461 CH CF₃ 0 O

124-126 462 CH CF₃ 0 O CH₂CON(2-OCH₃-5-Ph)C₆H₃ 167-169 463 CH CF₃ 0 O

157-158 464 CH CF₃ 0 O CH₂CON—(3-NO₂-4-Cl)C₆H₃ oil 465 CH CF₃ 0 O CH₂CON—(2-Cl-4-CH₃)C₆H₃ 106-108 466 CH CF₃ 0 O CH₂CON—(3-OCH₂CH₃)C₆H₄ waxy 467 CH CF₃ 0 O

169-171 468 CH CF₃ 0 O CH₂CON—(4-CH₃)C₆H₄ 139-141 469 CH CF₃ 0 O CH₂CON—(1-Naphthyl) 155-157 470 CH CF₃ 0 O CH₂CON—(3-I)C₆H₄ 135-137 471 CH CF₃ 0 O CH₂CON—(2-OCH₂CH₃)C₆H₄ 138 472 CH CF₃ 0 O CH₂CON—(2-OCH₃)C₆H₄ 130-132 473 CH CF₃ 0 O CH₂CON—[3,5-(OCH₃)₂]C₆H₃ 130-132 474 CH CF₃ 0 O CH₂CON—(4-Cl)C₆H₄ 139-141 475 CH CF₃ 0 O CH₂CON—(3-CH₃)C₆H₄ oil 476 CH CF₃ 0 O CH₂CON—(3-OCH₃)C₆H₄ oil 477 CH CF₃ 0 O CH₂CON—(4-CH₂CH₃)C₆H₄ 122-123 478 CH CF₃ 0 O CH₂CON—(4-CF₃)C₆H₄ 151-152 479 CH CF₃ 0 O CH₂CON—(2-CH₃-4-Cl)C₆H₃ 165-167 480 CH CF₃ 0 O CH₂CH₂NCH₂C₆H₅ oil 481 CH CF₃ 0 O CH₂CH₂NCH₂—(3-Pyridyl) oil 482 CH CF₃ 0 O CH₂CH═NOCH₂CH₃ oil 483 CH CF₃ 0 O CH₂CH═NOC₆H₅ oil 484 CH CF₃ 0 O CH₂CON—(4-NO₂)C₆H₄ 181-183 485 CH CF₃ 0 O CH₂CON—(2-CH₃-4-NO₂)C₆H₃ 129-131 486 CH CF₃ 0 O CH₂CON—(2-Cl-3-CF₃)C₆H₃ 136 487 CH CF₃ 0 O CH₂CON—(2-CN-4-Cl)C₆H₃ 157-159 488 CH CF₃ 0 O CH₂CON—(3,5-Cl₂)C₆H₃ 167-169 489 CH CF₃ 0 O CH₂CON—(3,5-Cl₂-4-OCF₂CHF₂)C₆H₂ 132-134 490 CH CF₃ 0 O CH₂CON—(2,4,5-Cl₃)C₆H₂ 146 491 CH CF₃ 0 O CH₂CON—(3,5-Cl₂-4-OCF₂CHFCF₃)C₆H₂ 124-126 492 CH CF₃ 0 O CH₂CON—(2-CF₃-4-Cl)C₆H₃ 136 493 CH CF₃ 0 O

oil 494 CH CF₃ 0 O

91-93 495 CH CF₃ 0 O

123-125 496 CH CF₃ 0 O

81-83 497 CH CF₃ 0 O

113-115 498 CH CF₃ 0 O COOH 155-157 499 CH CF₃ 0 O 4-F-C₆H₄ 104-106 500 CH CF₃ 0 O CON(C₂H₅)₂ oil 501 CH CF₃ 0 O CONCH(CH₃)₂ oil 502 CH CF₃ 0 O CON(CH₃)₂ 52-54 503 CH CF₃ 0 O CONHCH₂CCH 105-107 504 CH CF₃ 0 O CONH-cyclo-C₃H₅ 101-103 505 CH CF₃ 0 O CONH₂ 206-208 506 CH CF₃ 0 O

72-74 507 CH CF₃ 0 O

 98-100 508 CH CF₃ 0 O

108-110 509 CH CF₃ 0 O

140-142 510 CH CF₃ 0 O CONHCH₃ 127-129 511 CH CF₃ 0 O CONHCH₂CH═CH₂ oil 512 CH CF₃ 0 O CON(CH₂CN)₂ 90-92 513 CH CF₃ 0 O 4-(t-C₄H₉)—C₆H₄ 64-66 514 CH CF₃ 0 O 4-CF₃—C₆H₄ 89-91 515 CH CF₃ 0 O 4-CH₃-3-F—C₆H₃ 104-106 516 CH CF₃ 0 O 2,4-di-Cl—C₆H₃ 70-72 517 CH CF₃ 0 O 4-(NHSO₂CH₃)—C₆H₄ 204-206 518 CH CF₃ 0 O 2,6-di-Cl—C₆H₃ 139-141 519 CH CF₃ 0 O COOCH₂C₆H₅ 83-85 520 CH CF₃ 0 O CONHC₃H₇ oil 521 CH CF₃ 0 O 3,5-di-Br-4-(OCH₃)—C₆H₂ 132-134 522 CH CF₃ 0 O CHCl₂ oil 523 CH CF₃ 0 O CCl₃ oil 524 CH CF₃ 0 O CH(OCH₃)₂ oil 525 CH CF₃ 0 O 3-CF₃—C₆H₄ 57-59 526 CH CF₃ 0 O CON(CH₂)₅ oil 527 CH CF₃ 0 O CON(CH₃)CH₂C₆H₅ oil 528 CH CF₃ 0 O CONHCH₂C₆H₅ 96-98 529 CH CF₃ 0 O

oil 530 CH CF₃ 0 O CONH-n-C₆H₁₃ oil 531 CH CF₃ 0 O CON(CH₂CH₃)CH₂C₆H₅ oil 532 CH CF₃ 0 O CONH-c-C₆H₁₁ 115-117 533 CH CF₃ 0 O CON(n-C₄H₉)₂ oil 534 CH CF₃ 0 O

oil 535 CH CF₃ 0 O CONH-i-C₄H₉ oil 536 CH CF₃ 0 O

oil 537 CH CF₃ 0 O CON(CH₂)₄ 68-70 538 CH CF₃ 0 O CON(CH₃)n-C₆H₁₃ oil 539 CH CF₃ 0 O

oil 540 CH CF₃ 0 O CON(CH₃)CH₂CH₃ oil 541 CH CF₃ 0 O CONHOCH₃ oil 542 CH CF₃ 0 O

oil 543 CH CF₃ 0 O CON(CH₃)CH₂CH₂CH₃ oil 544 CH CF₃ 0 O CONHCH₂CH(OCH₃)₂ oil 545 CH CF₃ 0 O CONH-t-C₄H₉ 113-115 546 CH CF₃ 0 O CONHCH₂-4-Cl—C₆H₄ oil 547 CH CF₃ 0 O CONHCH(CH₃)C₆H₅ oil 548 CH CF₃ 0 O CONHCH₂CH₂OCH₃ 92-94 549 CH CF₃ 0 O

190-192 550 CH CF₃ 0 O CONHC(CH₃)₂CCH 90-92 551 CH CF₃ 0 O CONHCH₂-2-Furyl 93-95 552 CH CF₃ 0 O CON(CH₂)₃ 91-93 553 CH CF₃ 0 O CONHCH₂-c-C₃H₅ oil 554 CH CF₃ 0 O CONHC(CH₃)₂CH₂CH₃ oil 555 CH CF₃ 0 O CONH(CH₂)₃C₆H₅ oil 556 CH CF₃ 0 O CONHCH₂-3-Pyridyl 132-134 557 CH CF₃ 0 O CON(CH₃)-n-C₄H₉ oil 558 CH CF₃ 0 O CON(CH₂CH₃)-i-C₃H₇ oil 559 CH CF₃ 0 O

oil 560 CH CF₃ 0 O CONHCH₂CH₂Cl oil 561 CH CF₃ 0 O CONHCH₂CN 152-157 562 CH CF₃ 0 O CON(CH₃)OCH₃ oil 563 CH CF₃ 0 O CON(CH₃)CH₂CH═CH₂ oil 564 CH CF₃ 0 O CONHCH₂COOCH₃ oil 565 CH CF₃ 0 O CON(CH₃)-i-C₃H₇ oil 566 CH CF₃ 0 O CON(CH₃)CH₂CH₂CN oil 567 CH CF₃ 0 O CON(CH₃)CH₂CH(OCH₃)₂ oil 568 CH CF₃ 0 O CON(CH₃)CH₂CH(—CH₂CH₂O—) oil 569 CH CF₃ 0 O CONHCH₂C(═CH₂)CHH₃ oil 570 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH═CH₂ oil 571 CH CF₃ 0 O CONHC₆H₅ 83-85 572 CH CF₃ 0 O CON(CH₃)CH₂CCH oil 573 CH CF₃ 0 O CON(CH₃)CH₂CN oil 574 CH CF₃ 0 O CON(CH₃)CH₂CH₂N(CH₃)₂ oil 575 CH CF₃ 0 O CONHOCH₂CH₃ 114-116 576 CH CF₃ 0 O CONHCH₂CF₃ 74-76 577 CH CF₃ 0 O CON(CH₂CH₂Cl)₂ oil 578 CH CF₃ 0 O CONH-c-C₄H₇ oil 579 CH CF₃ 0 O CON(CH₂CH₂CH₃)CH₂-c-C₃H₅ oil 580 CH CF₃ 0 O CON(CH₃)-c-C₆H₁₁ oil 581 CH CF₃ 0 O CON(CH₂CH₃)CH₂C(═CH₂)CH₃ oil 582 CH CF₃ 0 O CONHOCH₂CH═CH₂ 90-92 583 CH CF₃ 0 O CONHOCH₂C₆H₅ 126-128 584 CH CF₃ 0 O CON(CH₃)CH₂COOCH₃ oil 585 CH CF₃ 0 O COONHCH₃ 230-232 586 CH CF₃ 0 O CONHCH₂CH₃ 83-85 587 CH CF₃ 0 O CONHCH(CH₃)COOCH₃ 104-106 588 CH CF₃ 0 O CONHCH(i-C₃H₇)COOCH₃ oil 589 CH CF₃ 0 O CON(CH₃)CH₂CON(CH₃)₂ oil 590 CH CF₃ 0 O CON(CH₃)-t-C₄H₉ oil 591 CH CF₃ 0 O CONHO-t-C₄H₉ 103-105 592 CH CF₃ 0 O CON(CH₃)CH(i-C₃H₇)COOCH₃ oil 593 CH CF₃ 0 O CH(OCH₂CH₃)₂ oil 594 CH CF₃ 0 O

oil 595 CH CF₃ 0 O

oil 596 CH CF₃ 0 O

oil 597 CH CF₃ 0 O

oil 598 CH CF₃ 0 O

oil 599 CH CF₃ 0 O CONHCH₂CONHCH₃ 101-103 600 CH CF₃ 0 O CON(CH₂)₇ oil 601 CH CF₃ 0 O CON(CH₂)₆ oil 602 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH₂OCH₃ oil 603 CH CF₃ 0 O

oil 604 CH CF₃ 0 O

oil 605 CH CF₃ 0 O

oil 606 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH₂CN oil 607 CH CF₃ 0 O

oil 608 CH CF₃ 0 O CON(CH₂CH₃)-n-C₄H₉ oil 609 CH CF₃ 0 O

179-181 610 CH CF₃ 0 O CONHCH(CH₃)CONHCH₃ 136-138 611 CH CF₃ 0 O COON(CH₂)₄ 64-66 612 CH CF₃ 0 O CONHCH₂CON(CH₃)₂ 107-109 613 CH CF₃ 0 O CON(CH₂COOCH₂CH₃)₂ oil 614 CH CF₃ 0 O

180-182 615 CH CF₃ 0 O

221-223 616 CH CF₃ 0 O

234-236 617 CH CF₃ 0 O

oil 618 CH CF₃ 0 O CON(CH₃)CH₂-6-Cl-3-pyridyl oil 619 CH CF₃ 0 O

105-107 620 CH CF₃ 0 O CONHCH(CH₃)CH(OCH₃)₂ oil 621 CH CF₃ 0 O CONHCH₂CH₂SCH₃ oil 622 CH CF₃ 0 O CONHCH(CH₃)CH₂OCH₃ 70-72 623 CH CF₃ 0 O CONHCH₂CH₂NHCOCH₃ 124-126 624 CH CF₃ 0 O CONH(CH₂)₃OCH₂CH₃ oil 625 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH₂CH₃ oil 626 CH CF₃ 0 O CON(CH₂CH₃)CH₂OCH₃ oil 627 CH CF₃ 0 O CONHCH₂CH₂SCH₂CH₃ oil 628 CH CF₃ 0 O CONHCH₂CH₂OCH₂CH₃ 59-61 629 CH CF₃ 0 O

oil 630 CH CF₃ 0 O

174-176 631 CH CF₃ 0 O CONHCH(CH₃)CH(OCH₃)₂ oil 632 CH CF₃ 0 O CONHCH₂CH₂SCH₃ oil 633 CH CF₃ 0 O CONHCH(CH₃)CH₂OCH₃ 70-72 634 CH CF₃ 0 O CONHCH₂CH₂NHCOCH₃ 124-126 635 CH CF₃ 0 O CONH(CH₂)₃OCH₂CH₃ oil 636 CH CF₃ 0 O CON(CH₂CH₃)CH₂CH₂CH₃ oil 637 CH CF₃ 0 O CON(CH₂CH₃)CH₂OCH₃ oil 638 CH CF₃ 0 O CONHCH₂CH₂SCH₂CH₃ oil 639 CH CF₃ 0 O CONHCH(CH₃)CH₂COOCH₂CH₃ oil 640 CH CF₃ 0 O CONH-4-COOCH₃—C₆H₄ 189-191 641 CH CF₃ 0 O CONH-4-CONH₂—C₆H₄ 265-267 642 CH CF₃ 0 O CONHCH₂CH₂Br oil 643 CH CF₃ 0 O CONHCH₂CH═CHCH₂Cl oil 644 CH CF₃ 0 O CONH-4-CONHCH₃—C₆H₄ 219-221 645 CH CF₃ 0 O CONHCH₂CH₂CH₂Br oil 646 CH CF₃ 0 O CONHCH₂CH₂CH₂OCH₃ oil 647 CH CF₃ 0 O CONH-4-CH₂CH₃—C₆H₄ 97-99 648 CH CF₃ 0 O CONHCH₂CH₂OCH(CH₃)₂ oil 649 CH CF₃ 0 O CONHCH₂CH₂CH₂OCH₂CH₃ oil 650 CH CF₃ 0 O

oil 651 CH CF₃ 0 O

64-66 652 CH CF₃ 0 O

oil 653 CH CF₃ 0 O

oil 654 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₃ oil 655 CH CF₃ 0 O CH₂CON(CH₃)₂ 58-60 656 CH CF₃ 0 O CH₂CON(CH₂)₄ 101-103 657 CH CF₃ 0 O

oil 658 CH CF₃ 0 O

90-92 659 CH CF₃ 0 O CH₂CONHCH₂CH₃ 104-106 660 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂OH oil 661 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂CH₃ oil 662 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH(—OCH₂CH₂O—) oil 663 CH CF₃ 0 O CH₂CONHCH₂CH₃ 104-106 664 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂OH oil 665 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH₂CH₃ oil 667 CH CF₃ 0 O CH₂CON(CH₃)CH₂CH(—OCH₂CH₂O—) oil 668 CH CF₃ 0 O

79-81 669 CH CF₃ 0 O CH₂CONHCH₂CH₂SCH₃ 65-67 670 CH CF₃ 0 O CH₂CONHCH(CH₃)CH₂OCH₃ 86-88 671 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCO-c-C₄H₇ oil 672 CH CF₃ 0 O CH₂CONHCH₂CH₂Br 87-89 673 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCOC₆H₅ oil 674 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCO-c-C₃H₅ oil 675 CH CF₃ 0 O CONH-2-CH₃—C₆H₄ 104-106 676 CH CF₃ 0 O CH₂CON(i-C₃H₇)-4-F—C₆H₄ 102-104 677 CH CF₃ 0 O

oil 678 CH CF₃ 0 O

oil 679 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCONHC₆H₅ 100-102 680 CH CF₃ 0 O CON(CH₃)CH₂CH₂OCONHCH₂CH₃ oil 681 CH CF₃ 0 O CON(CH₃)CH₂CH₂OSO₂CH₃ oil 682 CH CF₃ 0 O CH₂CONH-c-C₄H₇ 133-135 683 CH CF₃ 0 O CH₂CONHCH₂CN 158-160

TABLE 2

No. X Y W R¹ m.p. [° C.] 684 N (CF₂)₃— O CH₃   CHF₂ 685 N (CF₂)₂— O CH₂CH₃ CF₃ 686 N (CF₂)₂— O COOCH₂CH₃ CF₃ 687 N (CF₂)₂— O OH CF₃ 688 N (CF₂)₂— O OCH₃ CF₃ 689 N CF₂CF₃ O CH₃ 690 N CF₂CF₃ O CH₂CH₃ 691 N CF₂CF₃ S CH₃ 692 N CF₂CF₃ S CH₂CH₃ 693 N CF₂CF₃ S (CH₂)₂CH₃ 694 CH CF₃ O CH₃ oil 695 CH CF₃ O CH₂CH₃ 696 CH CF₃ O (CH₂)₂CH₃ 697 CH CF₃ O CH(CH₃)₂ 698 CH CF₃ O (CH₂)₃CH₃ 699 CH CF₃ O CH(CH₃)CH₂CH₃ 700 CH CF₃ O CH₂CH(CH₃)₂ 701 CH CF₃ O C(CH₃)₃ oil 702 CH CF₃ O (CH₂)₄CH₃ 703 CH CF₃ O CH(CH₃)(CH₂)₂— CH₃ 704 CH CF₃ O (CH₂)₂CH(CH₃)₂ 705 CH CF₃ O CH₂C(CH₃)₃ 706 CH CF₃ O cyclo-C₅H₉ 707 CH CF₃ O cyclo-C₆H₁₁ 708 CH CF₃ O CHO 709 CH CF₃ O CH═CH₂ 710 CH CF₃ O CH₂CH═C(CH₃)₂ 711 CH CF₃ O CH₂CH═CH₂ 712 CH CF₃ O C(CH₃)═CH₂ 713 CH CF₃ O (CH₂)₅C═CH₂ 714 CH CF₃ O C(═CHCH₃)CH₃ 715 CH CF₃ O CH₂C≡CH 716 CH CF₃ O CH₂CH₂C≡CH 717 CH CF₃ O CH₂C≡CCH₂CH₃ 718 CH CF₃ O (CH₂)₄C≡CH 719 CH CF₃ O CHFCF₃ 720 CH CF₃ O COOCH₂CH₃ 721 CH CF₃ O CH₂CH₂OH 722 CH CF₃ O CH₂CH₂OCH₃ 723 CH CF₃ O CH₂COOC(CH₃)₃ 724 CH CF₃ O CH₂SC₆H₅ 725 CH CF₃ O CH₂CONHCH₃ 726 CH CF₃ O CH₂CH(OH)— CH₂OH 727 CH CF₃ O CH₂COCH₃ 728 CH CF₃ O COCH₃ 729 CH CF₃ O CH₂OC₆H₅ 730 CH CF₃ O COC₆H₅ 731 CH CF₃ O CF₂CH₃ 732 CH CF₃ O CH₂CN 733 CH CF₃ O CH₂CH(—O—)CH₂ 734 CH CF₃ O CH₂(4-OCH₃)— C₆H₅ 735 CH CF₃ O CH₂CH(OH)CH₂S— C₆H₅ 736 CH CF₃ O CH═CF₂ 737 CH CF₃ O CCl═CHCl 738 CH CF₃ O 2-Pyridyl 739 CH CF₃ O OC₆H₅ 740 CH CF₃ O OH 741 CH CF₃ O OCH₃ 742 CH CF₃ O OCH₂CH₃ 743 CH CF₃ O OCHF₂ 744 CH CF₃ O OCH₂C₆H₅ 745 CH CF₃ O SCH₃ 746 CH CF₃ O SC₆H₅ 747 CH CF₃ O NH₂ 748 CH CF₃ O NHCH₃ 749 CH CF₃ O NHCH₂CH₃ 750 CH CF₃ O N(CH₂CH₃)₂ 751 CH CF₃ O N(CH₂CN)₂ 752 CH CF₃ O N(CH₃)₂ 753 CH CF₃ O NHCOCH₃ 754 CH CF₃ O NHCOCH₂CH₃ 755 CH CF₃ O OSO₂CH₃ 756 CH CF₃ O SOCH₂(4-Br)— C₆H₄ 757 CH CF₃ O N(CH₃)COOCH₂— C₆H₅ 758 N CF₃ O CH₃ 759 N CF₃ O CH₂CH₃ 760 N CF₃ O (CH₂)₂CH₃ 761 N CF₃ O CH(CH₃)₂ 762 N CF₃ O (CH₂)₃CH₃ 763 N CF₃ O CH₂CH(CH₃)₂ 764 N CF₃ O C(CH₃)₃ 765 N CF₃ O CH₂C(CH₃)₃ 766 N CF₃ O cyclo-C₅H₉ 767 N CF₃ O cyclo-C₆H₁₁ 768 N CF₃ O CH₂C═C(CH₃)₂ 769 N CF₃ O CH₂CH₂C═CH₂ 770 N CF₃ O CH₂CH═CH₂ 771 N CF₃ O (CH₂)₅CH═CH₂ 772 N CF₃ O CH₂C≡CH 773 N CF₃ O CH₂C≡CCH₂CH₃ 774 N CF₃ O CHFCF₃ 775 N CF₃ O COOCH₂CH₃ 776 N CF₃ O CH₂CH₂OH 777 N CF₃ O CH₂CH₂OCH₃ 778 N CF₃ O CH₂COOC(CH₃)₃ 779 N CF₃ O CH₂SC₆H₅ 780 N CF₃ O CH₂CONHCH₃ 781 N CF₃ O CH₂CH(OH)— CH₂OH 782 N CF₃ O CHO 783 N CF₃ O COCH₃ 784 N CF₃ O CH₂OC₆H₅ 785 N CF₃ O COC₆H₅ 786 N CF₃ O CF₂CH₃ 787 N CF₃ O CH₂CN 788 N CF₃ O CH₂CH₂CN 789 N CF₃ O CH═CF₂ 790 N CF₃ O 2-Furyl 791 N CF₃ O OH 792 N CF₃ O OCH₃ 793 N CF₃ O OCH₂CH₃ 794 N CF₃ O OCHF₂ 795 N CF₃ O OCH₂C₆H₅ 796 N CF₃ O NH₂ 797 N CF₃ O NHCH₃ 798 N CF₃ O NHCH₂CH₃ 799 N CF₃ O N(CH₂CH₃)₂ 800 N CF₃ O N(CH₂CN)₂ 801 N CF₃ O N(CH₃)₂ 802 N CF₃ O NHCOCH₃ 803 N CF₃ O NHCOCH₂CH₃ 804 N CF₃ O OSO₂CH₃ 805 CH CF₃ S CH₃ 806 CH CF₃ S CH₂CH₃ 807 CH CF₃ S (CH₂)₂CH₃ 808 CH CF₃ S CHO 809 CH CF₃ S CHFCF₃ 810 CH CF₃ S CH₂C≡CH 811 CH CF₃ S COOCH₂CH₃ 812 CH CF₃ S CH₂COOC(CH₃)₃ 813 CH CF₃ S CH₂CN 814 N CF₃ S CH₃ 815 N CF₃ S CH₂CH₃ 816 N CF₃ S (CH₂)₂CH₃ 817 N CF₃ S CHFCF₃ 818 N CF₃ S CH₂CH₂OH 819 N CF₃ S CH₂COOC(CH₃)₃ 820 N CH₂CH₂— O CH₂CH₃ Cl 821 N CH₂CH₂— O NH₂ Cl 822 N CH₂Cl O CH₃ 823 CH CHF₂ O CH₃ 824 CH CHF₂ O CH₂CH₃ 825 CH CHF₂ O (CH₂)₂CH₃ 826 CH CHF₂ O CH₂C═CH₂ 827 CH CHF₂ O C(CH₃)═CH₂ 828 CH CHF₂ O COOCH₂CH₃ 829 CH CHF₂ O CH₂CONHCH₃ 830 CH CHF₂ O CF₂CH₃ 831 CH CHF₂ O CHO 832 CH CHF₂ O NH₂ 833 CH CHF₂ O NHCOCH₃ 834 N CHF₂ O CH₃ 835 N CHF₂ O CH₂CH₃ 836 N CHF₂ O CH(CH₃)(CH₂)₄— CH₃ 837 N CHF₂ O CH₂CH═CH₂ 838 N CHF₂ O COOCH₂CH₃ 839 N CHF₂ O NH₂

TABLE 3

No. X Y m V R¹ m.p. [° C.] 840 N (CF₂)₃CHF₂ 0 O CH₃ 841 N (CF₂)₂CF₃ 0 O CH₂CH₃ 842 N (CF₂)₂CF₃ 0 O COOCH₂CH₃ 843 N (CF₂)₂CF₃ 0 O SH 844 N (CF₂)₂CF₃ 0 O SCH₃ 845 N (CF₂)₂CF₃ 0 O SCH₂C≡CH 846 N CF₂CF₃ 0 O CH₃ 847 N CF₂CF₃ 0 O CH₂CH₃ 848 N CF₃ 0 O CH₃ 849 N CF₃ 0 O CH₂CH₃ 850 N CF₃ 0 O (CH₂)₂CH₃ 851 N CF₃ 0 O CH(CH₃)₂ 852 N CF₃ 0 O (CH₂)₃CH₃ 853 N CF₃ 0 O CH₂CH(CH₃)₂ 854 N CF₃ 0 O C(CH₃)₃ 855 N CF₃ 0 O CH₂C(CH₃)₃ 856 N CF₃ 0 O Cyclo-C₅H₉ 857 N CF₃ 0 O Cyclo-C₆H₁₁ 858 N CF₃ 0 O CH₂CH═C(CH₃)₂ 859 N CF₃ 0 O CH₂CH₂CH═CH₂ 860 N CF₃ 0 O CH₂CH═CH₂ 861 N CF₃ 0 O (CH₂)₅CH═CH₂ 862 N CF₃ 0 O CH₂C≡CH 863 N CF₃ 0 O CH₂C≡CCH₂CH₃ 864 N CF₃ 0 O CHFCF₃ 865 N CF₃ 0 O COOCH₂CH₃ 866 N CF₃ 0 O CH₂CH₂OH 867 N CF₃ 0 O CH₂CH₂OCH₃ 868 N CF₃ 0 O CH₂COOC(CH₃)₃ 869 N CF₃ 0 O CH₂SPh 870 N CF₃ 0 O CH₂CONHCH₃ 871 N CF₃ 0 O CH₂CH(OH)CH₂OH 872 N CF₃ 0 O CHO 873 N CF₃ 0 O COCH₃ 874 N CF₃ 0 O CH₂OC₆H₅ 875 N CF₃ 0 O COPh 876 N CF₃ 0 O CF₂CH₃ 877 N CF₃ 0 O CH₂CN 878 N CF₃ 0 O CH₂CH₂CN 879 N CF₃ 0 O CH═CF₂ 880 N CF₃ 0 O 2-Furyl 881 N CF₃ 0 O OH 882 N CF₃ 0 O OCH₃ 883 N CF₃ 0 O OCH₂CH₃ 884 N CF₃ 0 O OCHF₂ 885 N CF₃ 0 O OCH₂Ph 886 N CF₃ 0 O NH₂ 887 N CF₃ 0 O NHCH₃ 888 N CF₃ 0 O NHCH₂CH₃ 889 N CF₃ 0 O N(CH₂CH₃)₂ 890 N CF₃ 0 O N(CH₂CN)₂ 891 N CF₃ 0 O N(CH₃)₂ 892 N CF₃ 0 O NHCOCH₃ 893 N CF₃ 0 O NHCOCH₂CH₃ 894 N CF₃ 0 O OSO₂CH₃ 895 N CH₂CH₂Cl 0 O CH₂CH₃ 896 N CH₂CH₂Cl 0 O NH₂ 897 N CH₂Cl 0 O CH₃ 898 N CHF₂ 0 O CH₃ 899 N CHF₂ 0 O CH₂CH₃ 900 N CHF₂ 0 O CH(CH₃)(CH₂)₄CH₃ 901 N CHF₂ 0 O CH₂CH═CH₂ 902 N CHF₂ 0 O COOCH₂CH₃ 903 N CHF₂ 0 O NH₂ 904 CH CF₃ 0 O CH₃ 60-61 905 CH CF₃ 1 O CH₃ 906 CH CF₃ 0 O CH₂CH₃ oil 907 CH CF₃ 1 O CH₂CH₃ oil 908 CH CF₃ 0 O (CH₂)₂CH₃ oil 909 CH CF₃ 1 O (CH₂)₂CH₃ oil 910 CH CF₃ 0 O CH(CH₃)₂ 911 CH CF₃ 1 O CH(CH₃)₂ 912 CH CF₃ 0 O (CH₂)₃CH₃ 913 CH CF₃ 1 O (CH₂)₃CH₃ 914 CH CF₃ 0 O CH(CH₃)CH₂CH₃ 915 CH CF₃ 1 O CH(CH₃)CH₂CH₃ 916 CH CF₃ 0 O CH₂CH(CH₃)₂ 917 CH CF₃ 1 O CH₂CH(CH₃)₂ 918 CH CF₃ 0 O C(CH₃)₃ 919 CH CF₃ 1 O C(CH₃)₃ 920 CH CF₃ 0 O (CH₂)₄CH₃ 921 CH CF₃ 1 O (CH₂)₄CH₃ 922 CH CF₃ 0 O CH(CH₃)(CH₂)₂CH₃ 923 CH CF₃ 0 O (CH₂)₂CH(CH₃)₂ 924 CH CF₃ 0 O CH₂C(CH₃)₃ 925 CH CF₃ 0 O cyclo-C₅H₉ 926 CH CF₃ 0 O cyclo-C₆H₁₁ 927 CH CF₃ 0 O CH₂(3-Thienyl) oil 928 CH CF₃ 0 O CHO 929 CH CF₃ 0 O CH═CH₂ 930 CH CF₃ 0 O CH₂Ph 61-63 931 CH CF₃ 0 O CH₂CH═C(CH₃)₂ 932 CH CF₃ 0 O CH₂CH═CH₂ 933 CH CF₃ 0 O C(CH₃)═CH₂ 934 CH CF₃ 0 O (CH₂)₅C═CH₂ 935 CH CF₃ 0 O C(═CHCH₃)CH₃ 936 CH CF₃ 0 O CH₂C≡CH 937 CH CF₃ 0 O CH₂CH₂C≡CH₂ 938 CH CF₃ 0 O CH₂C≡CCH₂CH₃ 939 CH CF₃ 0 O (CH₂)₄C≡CH 940 CH CF₃ 0 O CHFCF₃ 941 CH CF₃ 0 O COOCH₂CH₃ 942 CH CF₃ 0 O CH₂CH₂OH 943 CH CF₃ 0 O CH₂CH₂OCH₃ 944 CH CF₃ 0 O CH₂COOC(CH₃)₃ 945 CH CF₃ 0 O CH₂SPh 946 CH CF₃ 0 O CH₂CONHCH₃ 947 CH CF₃ 0 O CH₂CH(OH)CH₂OH 948 CH CF₃ 0 O CH₂COCH₃ 949 CH CF₃ 0 O COCH₃ 950 CH CF₃ 0 O CH₂Oph 951 CH CF₃ 0 O COPh 952 CH CF₃ 0 O CF₂CH₃ 953 CH CF₃ 0 O CH₂CN oil 954 CH CF₃ 0 O CH₂CH(—O—)CH₂ 955 CH CF₃ 0 O CH₂(4-OCH₃)Ph 956 CH CF₃ 0 O CH₂CH(OH)CH₂SPh 957 CH CF₃ 0 O CH═CF₂ 958 CH CF₃ 0 O CCl═CHCl 959 CH CF₃ 0 O Ph 120-121 960 CH CF₃ 0 O 2-Thienyl 87-89 961 CH CF₃ 0 O Oph 962 CH CF₃ 0 O OH 963 CH CF₃ 0 O OCH₃ 964 CH CF₃ 0 O OCH₂CH₃ 965 CH CF₃ 0 O OCHF₂ 966 CH CF₃ 0 O OCH₂Ph 967 CH CF₃ 0 O SCH₃ 968 CH CF₃ 0 O SPh 969 CH CF₃ 0 O NH₂ 190-191 970 CH CF₃ 0 O NHCH₃ 971 CH CF₃ 0 O NHCH₂CH₃ 972 CH CF₃ 0 O N(CH₂CH₃)₂ 973 CH CF₃ 0 O N(CH₂CN)₂ 974 CH CF₃ 0 O N(CH₃)₂ 975 CH CF₃ 0 O NHCOCH₃ 976 CH CF₃ 0 O NHCOCH₂CH₃ 977 CH CF₃ 0 O OSO₂CH₃ 978 CH CF₃ 0 O SOCH₂(4-Br)—C₆H₄ 979 CH CF₃ 0 O N(CH₃)COOCH₂Ph 980 CH CF₃ 0 NCH₃ CH₃ 981 CH CF₃ 0 NCH₂CH₃ CH₃ 982 CH CF₃ 0 NCH₂CH₃ CH₂CH₃ 983 CH CF₃ 0 NCH₂CN CH₂CH₃ 984 CH CF₃ 0 NCH₂OCH₃ NHCH₃ 985 CH CF₃ 0 NCH₂OCH₂CH₃ CN 986 CH CF₃ 0 NCH₂CH═CH₂ CH₃ 987 CH CF₃ 0 NCH₂CH═CF₂ SCH₃ 988 CH CF₃ 0 NCH₂OCH₃ SCH₂CH₃ 989 CH CF₃ 0 NCH₂OCH₃ SCH₂Ph 990 CH CHF₂ 0 O CH₃ 991 CH CHF₂ 0 O CH₂CH₃ 992 CH CHF₂ 0 O (CH₂)₂CH₃ 993 CH CHF₂ 0 O CH₂CH═CH₂ 994 CH CHF₂ 0 O C(CH₃)═CH₂ 995 CH CHF₂ 0 O COOCH₂CH₃ 996 CH CHF₂ 0 O CH₂CONHCH₃ 997 CH CHF₂ 0 O CF₂CH₃ 998 CH CHF₂ 0 O CHO 999 CH CHF₂ 0 O NH₂ 1000 CH CHF₂ 0 O NHCOCH₃ 1001 N CF₂CF₃ 0 S CH₃ 1002 N CF₂CF₃ 0 S CH₂CH₃ 1003 N CF₂CF₃ 0 S (CH₂)₂CH₃ 1004 N CF₃ 0 S CH₃ 1005 N CF₃ 0 S CH₂CH₃ 1006 N CF₃ 0 S (CH₂)₂CH₃ 1007 N CF₃ 0 S CHFCF₃ 1008 N CF₃ 0 S CH₂CH₂OH 1009 N CF₃ 0 S CH₂COOC(CH₃)₃ 1010 CH CF₃ 0 S CH₃ 1011 CH CF₃ 0 S CH₂CH₃ 1012 CH CF₃ 0 S (CH₂)₂CH₃ 1013 CH CF₃ 0 S CHO 1014 CH CF₃ 0 S CHFCF₃ 1015 CH CF₃ 0 S CH₂C≡CH 1016 CH CF₃ 0 S COOCH₂CH₃ 1017 CH CF₃ 0 S CH₂COOC(CH₃)₃ 1018 CH CF₃ 0 S CH₂CN

TABLE 4

m.p. No. X Y m V R² R³ [° C.] 1019 N (CF₂)₃ 0 S H CH₂CH₃ CHF₂ 1020 N CF₂CF₂CF₃ 0 S H CH₂CH₃ 1021 N CF₂CF₃ 0 S H CH₂CH₃ 1022 N CH₂CH₂Cl 0 S H CH₂CH₃ 1023 N CH₂Cl 0 S H CH₂CH₃ 1024 N CF₃ 0 S CH₂CH₃ CH₂CH₃ 1025 N CF₃ 0 S (CH₂)₂CH₃ H 1026 N CF₃ 0 S CH(CH₃)₂ H 1027 N CF₃ 0 S CH₂CH(CH₃)₂ H 1028 N CF₃ 0 S C(CH₃)₃ H 1029 CH CF₃ 0 S H CH₃ oil 1030 CH CF₃ 0 S H CH₂CH₃ oil 1031 CH CF₃ 0 S H C(CH₃)₃ oil 1032 CH CF₃ 0 S CH₂CH₃ COOCH₂CH₃ 1033 CH CF₃ 0 S (CH₂)₂CH₃ COOCH₂CH₃ 1034 CH CF₃ 0 S CH(CH₃)₂ COOCH₂CH₃ 1035 CH CF₃ 0 S CH(CH₃)₂ CONHCH₂CH₃ 1036 CH CF₃ 0 S CH(CH₃)₂ CONHCH₂CH₃ 1037 CH CF₃ 0 S CH(CH₃)₂ CON(CH₂CH₃)₂ 1038 CH CF₃ 0 S CH(CH₃)₂ CONH-cyclo-C₃H₇ 1039 CH CF₃ 0 S C(CH₃)₃ COOCH₂CH₃ 1040 CH CF₃ 0 S H CONHCH₂CH₃ 1041 CH CF₃ 0 S H CON(CH₂CH₃)₂ 1042 CH CF₃ 0 S H COOCH₂CH₃ oil 1043 CH CF₃ 0 S H CH₂COOCH₂CH₃ oil 1044 CH CF₃ 0 S H CH₂CHO 1045 CH CF₃ 0 S H CH₂OCH₃ 1046 CH CF₃ 0 S H CH₂OCH₂Ph 1047 CH CF₃ 0 S H H 1048 CH CF₃ 0 S cyclo-C₅H₉ H 1049 CH CF₃ 0 S CON(CH₃)₂ CH₃ oil 1050 CH CF₃ 0 S CH₃ CH₂CH₂OH 1051 CH CF₃ 0 S CH₃ CH₂CH₂OCH₃ 1052 CH CF₃ 0 S CH₃ CH₂CH₂OCH₂Ph 1053 CH CF₃ 0 S CH₃ CH₂CH₂SPh 1054 CH CF₃ 0 S CH₃ CH₃ oil 1055 CH CF₃ 0 S CH₃ CH₂CH₂CHO 1055 CH CF₃ 0 S CH₃ CH₂CH₂CHNPh 1057 CH CF₃ 0 S CH₃ CH₂CH₂CONH₂ 1058 CH CF₃ 0 S H (4-CF₃O)C₆H₄ 120- 121 1059 CH CF₃ 0 S CH₂C≡CH H 1060 CH CF₃ 0 S CH₂CH₂C≡CH H 1061 CH CF₃ 0 S CH₂C≡CCH₂CH₃ H 1062 CH CF₃ 0 S CH₂CH═C(CH₃)₂ H 1063 CH CF₃ 0 S CH₂CH₂CH═CH₂ H 1064 CH CF₃ 0 S CH₂CH═CH₂ H 1065 CH CF₃ 0 S C(CH₃)═CH₂ H 1066 CH CF₃ 0 S CHFCF₃ H 1067 CH CF₃ 0 S COOCH₂CH₃ H 1068 CH CF₃ 0 S CH₂CH₂OH H 1069 CH CF₃ 0 S CH₂CH₂OCH₃ H 1070 CH CF₃ 0 S CH₂COOC(CH₃)₃ H 1071 CH CF₃ 0 S CH₂COCH₃ H 1072 CH CF₃ 0 S COCH3 H 1073 CH CF₃ 0 S CH₂Oph H 1074 CH CF₃ 0 S COPh H 1075 CH CF₃ 0 S CO(4-Cl)-C₆H₄ H 1076 CH CF₃ 0 S CF₂CH₃ H 1077 CH CF₃ 0 S CH₂CN H 1078 CH CF₃ 0 S CH₂CH₂CN H 1079 N CF₃ 0 S H H 1080 N CF₃ 0 S H CH₂CH₂CN 1081 N CF₃ 0 S H CH₂CO₂C(CH₃)₃ 1082 N CF₃ 0 S H CH₂CHO 1083 N CF₃ 0 S H CH₂CH₂OH 1084 N CF₃ 0 S H CH₂CH₂OCH₃ 1085 N CF₃ 0 S cyclo-C₅H₉ H 1086 N CF₃ 0 S CH₃ COOCH₂CH₃ 1087 N CF₃ 0 S CH₃ COOH 1088 N CF₃ 0 S CH₃ CONH₂ 1089 N CF₃ 0 S CH₃ CONHCH₂CH₃ 1090 N CF₃ 0 S CH₃ CON(CH₂CH₃)₂ 1091 N CF₃ 0 S CH₃ CONHCH₃ 1092 N CF₃ 0 S CH₃ CONHCH₂CN 1093 N CF₃ 0 S CH₃ CON(CH₂CN)₂ 1094 N CF₃ 0 S CH₃ CON(CH₃)₂ 1095 N CF₃ 0 S CH₂C≡CH OCH₂CH₃ 1096 N CF₃ 0 S CH₂CH₂C≡CH OCH₂CH₃ 1097 N CF₃ 0 S CH₂C≡CCH₂CH₃ OCH₂CH₃ 1098 N CF₃ 0 S CH₂CH═C(CH₃)₂ OCH₂CH₃ 1099 N CF₃ 0 S CH₂CH₂CH═CH₂ OCH₂CH₃ 1100 N CF₃ 0 S CH₂CH═CH₂ OCH₂CH₃ 1101 N CF₃ 0 S C(CH₃)═CH₂ OCH₂CH₃ 1102 N CF₃ 0 S CHFCF₃ OCH₂CH₃ 1103 N CF₃ 0 S COOCH₂CH₃ OCH₂CH₃ 1104 N CF₃ 0 S CH₂CH₂OH OCH₂CH₃ 1105 N CF₃ 0 S CH₂CH₂OCH₃ OCH₂CH₃ 1106 N CF₃ 0 S CH₂COOC(CH₃)₃ OCH₂CH₃ 1107 N CF₃ 0 S CH₂COCH₃ H 1108 N CF₃ 0 S COCH₃ H 1109 N CF₃ 0 S CH₂Oph H 1110 N CF₃ 0 S COPh H 1111 N CF₃ 0 S CO(4-Cl)-C₆H₄ H 1112 N CF₃ 0 S CF₂CH₃ H 1113 N CF₃ 0 S CH₂CN H 1114 N CF₃ 0 S CH₂CH₂CN H 1115 CH CF₃ 0 O CH₂CH₃ CH₂CH₃ 1116 CH CF₃ 0 O (CH₂)₂CH₃ H 1117 CH CF₃ 0 O H CH₂CH₃ oil 1118 CH CF₃ 0 O CH(CH₃)₂ COOCH₂CH₃ 1119 CH CF₃ 0 O CH(CH₃)₂ COOH 1120 CH CF₃ 0 O CH(CH₃)₂ CONH₂ 1121 CH CF₃ 0 O CH(CH₃)₂ CH₃ 1122 CH CF₃ 0 O C(CH₃)₃ H 1123 CH CF₃ 0 O H CH₃ 1124 CH CF₃ 0 O H cyclo-C₅H₉ 1125 CH CF₃ 0 O H CH₂CH₂CH₃ 1126 CH CF₃ 0 O H Ph 103- 104 1127 CH CF₃ 0 O H 2-Pyridyl 1128 CH CF₃ 0 O H 2-Furyl 1129 CH CF₃ 0 O cyclo-C₅H₉ H 1130 CH CF₃ 0 O CH₃ COOCH₂CH₃ 1131 CH CF₃ 0 O CH₃ COOH 1132 CH CF₃ 0 O CH₃ CONH₂ 1133 CH CF₃ 0 O CH₃ CONHCH₂CH₃ 1134 CH CF₃ 0 O CH₃ CON(CH₂CH₃)₂ 1135 CH CF₃ 0 O CH₃ CONHCH₃ 1136 CH CF₃ 0 O CH₃ CONHCH₂CN 1137 CH CF₃ 0 O CH₃ CON(CH₂CN)₂ 1138 CH CF₃ 0 O CH₃ CON(CH₃)₂ 1139 CH CF₃ 0 O CH₂C≡CH H 1140 CH CF₃ 0 O CH₂CH₂C≡CH H 1141 CH CF₃ 0 O CH₂C≡CCH₂CH₃ H 1142 CH CF₃ 0 O CH₂CH═C(CH₃)₂ H 1143 CH CF₃ 0 O CH₂CH₂C═CH H 1144 CH CF₃ 0 O CH₂CH═CH₂ H 1145 CH CF₃ 0 O C(CH₃)═CH₂ H 1146 CH CF₃ 0 O CHFCF₃ H 1147 CH CF₃ 0 O COOCH₂CH₃ H 1148 CH CF₃ 0 O CH₂CH₂OH H 1149 CH CF₃ 0 O CH₂CH₂OCH₃ H 1150 CH CF₃ 0 O CH₂COOC(CH₃)_(3 H) 1151 CH CF₃ 0 O CH₂COCH₃ H 1152 CH CF₃ 0 O COCH₃ H 1153 CH CF₃ 0 O CH₂OPh H 1154 CH CF₃ 0 O COPh H 1155 CH CF₃ 0 O CO(4-Cl)-C₆H₄ H 1156 CH CF₃ 0 O CF₂CH₃ H 1157 CH CF₃ 0 O CH₂CN H 1158 CH CF₃ 0 O CH₂CH₂CN H 1159 N CF₃ 0 O CH₂CH₃ CH₂CH₃ 1160 N CF₃ 0 O (CH₂)₂CH₃ H 1161 N CF₃ 0 O CH(CH₃)₂ CONH₂ 1162 N CF₃ 0 O CH(CH₃)₂ CH₃ 1163 N CF₃ 0 O C(CH₃)₃ H 1164 N CF₃ 0 O H CH₃ 1165 N CF₃ 0 O H CH₂CH₃ 1166 N CF₃ 0 O H CH₂CH₂CH₃ 1167 N CF₃ 0 O H Ph 1168 N CF₃ 0 O H 2-Pyridyl 1169 N CF₃ 0 O H 2-Furyl 1170 N CF₃ 0 O cyclo-C₅H₉ H 1171 N CF₃ 0 O CH₃ COOCH₂CH₃ 1172 N CF₃ 0 O CH₃ COOH 1173 N CF₃ 0 O CH₃ CONH₂ 1174 N CF₃ 0 O CH₃ CONHCH₂CH₃ 1175 N CF₃ 0 O CH₃ CON(CH₂CH₃)₂ 1176 N CF₃ 0 O CH₃ CONHCH₃ 1177 N CF₃ 0 O CH₃ CONHCH₂CN 1178 N CF₃ 0 O CH₃ CON(CH₂CN)2 1179 N CF₃ 0 O CH₃ CON(CH₃)₂ 1180 N CF₃ 0 O CH₂C≡CH H 1181 N CF₃ 0 O CH₂CH₂C≡CH H 1182 N CF₃ 0 O CH₂C≡CCH₂CH₃ H 1183 N CF₃ 0 O CH₂CH═C(CH₃)₂ H 1184 N CF₃ 0 O CH₂CH₂CH═CH₂ H 1185 N CF₃ 0 O CH₂CH═CH₂ H 1186 N CF₃ 0 O C(CH₃)═CH₂ H 1187 N CF₃ 0 O CHFCF₃ H 1188 N CF₃ 0 O COOCH₂CH₃ H 1189 N CF₃ 0 O CH₂CH₂OH H 1190 N CF₃ 0 O CH₂CH₂OCH₃ H 1191 N CF₃ 0 O CH₂COOC(CH₃)₃ H 1192 N CF₃ 0 O CH₂COCH₃ H 1193 N CF₃ 0 O COCH₃ H 1194 N CF₃ 0 O CH₂Oph H 1195 N CF₃ 0 O COPh H 1196 N CF₃ 0 O CO(4-Cl)-C₆H₄ H 1197 N CF₃ 0 O CF₂CH₃ H 1198 N CF₃ 0 O CH₂CN H 1199 N CF₃ 0 O CH₂CH₂CN H 1200 N CF₃ 0 O CH₂NHSO₂CH₃ CH₃ 1201 N CF₃ 0 O (CH₂)₂NHSO₂— CH₃ CH₃ 1202 N CF₃ 0 O CH₂NHSO₂CH₂— CH₃ CH₃ 1203 N CF₃ 0 O H CH₂NHSO₂CH₂Ph 1204 CH CF₃ 0 O (CH₂)₄NHSO₂— CH₃ CF₃ 1205 CH CF₃ 0 O (CH₂)₂S(CH₂)₂— CH₂CH₂CH₃ CH₃ 1206 CH CF₃ 0 O (CH₂)₄S(CH₂)₄— CH₃ OCH₃ 1207 CH CF₃ 0 S CH₃ (CH₂)₂S(CH₂)₂CN 1208 CH CF₃ 0 S CH₂NHSO₂— CH₃ CH₂CH₃ 1209 CH CF₃ 0 S CH₂NHSO₂— CH₂CH₂CH₃ CH₂Ph 1210 CH CF₃ 0 S (CH₂)₂NHSO₂— CF₃ CH₃ 1211 CH CF₃ 0 S H CH₂NHSO₂CH₃ 1212 CH CF₃ 0 S CH(CH₃)CH₂NH— CF₃ Ph 1213 CH CF₃ 0 S (CH₂)₂S(2-F)— CH₂CH₂CH₃ C₆H₄ 1214 CH CF₃ 0 S (CH₂)₆NHCH₂)₆— CF₃ OCH₃ 1215 CH CF₃ 0 S H (CH₂)₂NH-(2-F)— C₆H₄ 1216 CH CF₃ 0 S (CH₂)₃NHCH₂CN H 1217 CH CF₃ 0 S (CH₂)₂O(3-Cl)— CH₃ C₆H₄ 1218 CH CF₃ 0 S CF₃ (CH₂)₆NHCH₂CF₃ 1219 CH CF₃ 0 S CH₃ (CH₂)₂O(3-CH₃)— C₆H₄ 1220 CH CF₃ 0 O H CH₂NHPh 1221 CH CF₃ 0 O CH₃ (CH₂)₄S(2-Br)— C₆H₄ 1222 CH CF₃ 0 O (CH₂)₆NH(CH₂)₂ CH₃ OCH₃ 1223 CH CF₃ 0 O (CH₂)₂NH(CH₂)₄ H OCH₃ 1224 CH CF₃ 0 O CF₃ (CH₂)₃NH-(4-CN)— C₆H₄ 1225 CH CF₃ 0 O (CH₂)₄NHCH₂— CH₃ CF₃ 1226 CH CF₃ 0 O C₂F₅ (CH₂)₂O(3-CH₃)— C₆H₄ 1227 CH CF₃ 0 O (CH₂)₄NHCH₂CN H 1228 CH CF₃ 0 O (CH₂)₃O(4-Cl)— C₂F₅ C₆H₄

TABLE 5

m.p. No. X Y V R⁴ R⁵ R⁶ R⁷ [° C.] 1229 CH CF₃ O H H H H oil 1230 CH CF₃ O H H CH₃ H oil 1231 CH CF₃ O H H CH₂CH₃ H oil 1232 CH CF₃ O H H CH(CH₃)₂ H 1233 CH CF₃ O H H CH₂CH(CH₃)₂ H 1234 CH CF₃ O H H CH(CH₃)CH₂— H CH₃ 1235 CH CF₃ O H H CH₂OH H 1236 CH CF₃ O H H CH(OH)CH₃ H 1237 CH CF₃ O H H CH₂SH H 1238 CH CF₃ O H H CH₂CH₂SCH₃ H 1239 CH CF₃ O H H (CH₂)₃NH₂ H 1240 CH CF₃ O H H (CH₂)₄NH₂ H 1241 CH CF₃ O H H CH═CH₂ H 1242 CH CF₃ O H H (CH₂)₂— H COOCH₃ 1243 CH CF₃ O H H (CH₂)₂COOH H 1244 CH CF₃ O H H (CH₂)₂CONH₂ H 1245 CH CF₃ S CH₃ CH₃ H H 1246 CH CF₃ O H H CH₃ CH₃ oil 1247 CH CF₃ O H H CH₂COOCH₃ H 1248 CH CF₃ O H H CH₂COOH H 1249 CH CF₃ O H H CH₂CONH₂ H 1250 CH CF₃ O H H CH₂Ph H 1251 CH CF₃ O H H CH₂-(4-OH)— H C₆H₄ 1252 CH CF₃ O H H CH₂-(3-indolyl) H 1253 CH CF₃ O CH₃ CH₃ H H oil 1254 CH CF₃ O CH₃ H H H oil 1255 CH CF₃ O CH₃ H H Ph 1256 CH CF₃ O H (CH₂)₄ H 1257 CH CF₃ NH H (CH₂)₄ H 1258 CH CF₃ NCH₃ H (CH₂)₄ H 1259 CH CF₃ NCH₂— H (CH₂)₄ H C₆H₄ 1260 CH CF₃ NCH— H (CH₂)₄ H (CH₃)₂ 1261 CH CF₃ O Ph H Ph H 1262 CH CF₃ NH Ph H Ph H 1263 CH CF₃ NCH₃ Ph H Ph H 1264 CH CF₃ NCH₂— Ph H Ph H C₆H₄ 1265 N CF₃ O H H CH₂CH₃ H oil 1266 N CF₃ O H H CH(CH₃)₂ H 1267 N CF₃ O H H CH₂CH(CH₃)₂ H 1268 N CF₃ O H H CH₂COOH H 1269 N CF₃ O H H CH₂COOCH₃ H 1270 N CF₃ O H H CH₂CONH₂ H 1271 N CF₃ O CH₃ CH₃ H H 1272 N CF₃ O H (CH₂)₄ H 1273 N CF₃ O H H CH₂CH₂SCH₃ H 1274 CH CF₃ S H H H H oil

TABLE 6

m.p. No. X Y R⁸ R¹ [° C.] 1275 CH CF₃ CH₃ SH 209- 210 1276 CH CF₃ CH₃ SCH₃ 1277 CH CF₃ CH₃ SCH₂CH₃ 1278 CH CF₃ CH₃ S(CH₂)₂CH₃ 1279 CH CF₃ CH₃ SCH(CH₃)₂ 1280 CH CF₃ CH₃ SPh 1281 CH CF₃ CH₃ S(CH₂)₃CH₃ 1282 CH CF₃ CH₃ SCH(CH₃)CH₂CH₃ 1283 CH CF₃ CH₃ SCH₂CH(CH₃)₂ 1284 CH CF₃ CH₃ OH 119- 120 1285 CH CF₃ CH₃ OCH₃ 1286 CH CF₃ CH₃ OCH₂CH₃ 1287 CH CF₃ CH₃ OCHF₂ 1288 CH CF₃ CH₃ OCH₂Ph 1289 CH CF₃ CH₃ OCONHPh 1290 CH CF₃ CH₃ OCONH-(4-F)—C₆H₄ 1291 CH CF₃ CH₃ OCONH-(3,5-di-Cl)—C₆H₃ 1292 CH CF₃ CH₂CN OCH₃ 1293 CH CF₃ CH₂CN OCH₂CH₃ 1294 CH CF₃ CH₂CN OCHF₂ 1295 CH CF₃ CH₂CN OCH₂Ph 1296 CH CF₃ CH₂CN OCONHPh 1297 CH CF₃ CH₂CN OCONH-(4-F)—C₆H₄ 1298 CH CF₃ CH₂OCH₂CH₃ OCH₃ 1299 CH CF₃ CH₂OCH₂CH₃ OCH₂CH₃ 1300 CH CF₃ CH₂OCH₂CH₃ OCHF₂ 1301 CH CF₃ CH₂OCH₂CH₃ OCH₂Ph 1302 CH CF₃ CH₂OCH₂CH₃ OCONHPh 1303 CH CF₃ H CH₃ 203- 204 1304 CH CF₃ H CH₂CH₃ 134- 135 1305 CH CF₃ H (CH₂)₂CH₃ 1306 CH CF₃ H CH(CH₃)₂ 1307 CH CF₃ H Cyclo-C₃H₅ 1308 CH CF₃ H (CH₂)₃CH₃ 1309 CH CF₃ H CH(CH₃)CH₂CH₃ 1310 CH CF₃ H CH₂CH(CH₃)₂ 1311 CH CF₃ H CH═CH₂ 1312 CH CF₃ H CH₂CH═C(CH₃)₂ 1313 CH CF₃ H CH₂CH₂CH═CH₂ 1314 CH CF₃ H CH₂CH═CH₂ 1315 CH CF₃ H C(CH₃)═CH₂ 1316 CH CF₃ H CHFCF₃ 1317 CH CF₃ H COOCH₂CH₃ 1318 CH CF₃ H CH₂CH₂OH 1319 CH CF₃ H CH₂CH₂OCH₃ 1320 CH CF₃ H CH₂COOC(CH₃)₃ 1321 CH CF₃ CH₃ CH₂COOC(CH₃)₃ 1322 CH CF₃ CH₂CN CH₂COOC(CH₃)₃ 1323 CH CF₃ CH₂OCH₂CH₃ CH₂COOC(CH₃)₃ 1324 CH CF₃ H CH₂SPh 1325 CH CF₃ H CH₂CONHCH₃ 1326 CH CF₃ H CH₂COCH₃ 1327 CH CF₃ H COCH3 1328 CH CF₃ H CH₂Oph 1329 CH CF₃ H COPh 1330 CH CF₃ H CO(3-Cl)— C₆H₄ 1331 CH CF₃ H CF₂CH₃ 1332 CH CF₃ H CH₂CN 1333 CH CF₃ H CH₂CH₂CN 1334 CH CF₃ H CH₂CH(—O—)CH₂ 1336 CH CF₃ H CH₂(4-OCH₃)Ph 1337 N CF₃ CH₃ SH 1338 N CF₃ CH₃ SCH₃ 1339 N CF₃ CH₃ SCH₂CH₃ 1340 N CF₃ CH₃ SPh 1341 N CF₃ CH₃ SCH₂CH(CH₃)₂ 1342 N CF₃ CH₃ OH 1343 N CF₃ CH₃ OCH₃ 1344 N CF₃ CH₃ OCH₂CH₃ 1345 N CF₃ CH₃ OCH₂Ph 1346 N CF₃ CH₃ OCONHPh 1347 N CF₃ CH₂CN OCH₃ 1348 N CF₃ CH₂CN OCH₂CH₃ 1349 N CF₃ CH₂CN OCH₂Ph 1350 N CF₃ CH₂CN OCONHPh 1351 N CF₃ CH₂OCH₂CH₃ OCH₃ 1352 N CF₃ CH₂OCH₂CH₃ OCH₂Ph 1353 N CF₃ CH₂OCH₂CH₃ OCONHPh 1354 N CF₃ H CH₃ 1355 N CF₃ H CH₂CH₃ 1356 N CF₃ H (CH₂)₂CH₃ 1357 N CF₃ H CH(CH₃)₂ 1358 N CF₃ H (CH₂)₃CH₃ 1359 N CF₃ H CH(CH₃)CH₂CH₃ 1360 N CF₃ H CH₂CH(CH₃)₂ 1361 N CF₃ H CH₂C═C(CH₃)₂ 1362 N CF₃ H CH₂CH═CH₂ 1363 N CF₃ H C(CH₃)H═CH₂ 1364 N CF₃ H COOCH₂CH₃ 1365 N CF₃ H CH₂CH₂OH 1366 N CF₃ H CH₂CH₂OCH₃ 1367 N CF₃ H CH₂COOC(CH₃)₃ 1368 N CF₃ H CH₂SPh 1369 N CF₃ H CH₂CONHCH₃ 1370 N CF₃ H CH₂COCH₃ 1371 N CF₃ H COCH₃ 1372 N CF₃ H CH₂Oph 1373 N CF₃ H COPh 1374 N CF₃ H CH₂CN 1375 N CF₃ H CH₂CH₂CN 1376 CH CF₃ CH₃ CH₂CH₃ oil

The insecticidally active compounds used according to the invention are known and commercially available.

Deltamethrin, endosulfan, triazaphos, amitraz, piperonyl butoxide and Bacillus thuringiensis, for example, are obtainable from Hoechst Schering AgrEvo GmbH, Berlin, Germany.

The compounds are furthermore described in detail in The Pesticide Manual, 11th ed., British Crop Protection Council, Farnham 1997. Instructions for their preparation are likewise given in this publication.

Baculum viruses are described, for example, in J. Ind. Microbiol. & Biotech. 1997, 19,192.

The compounds of group (f) are described in WO-A98/57 969, with preparation processes and use examples.

These sources and the literature cited therein are expressly referred to herewith; they are incorporated into this description by reference.

The insecticides used according to the invention are usually obtainable as commercial formulations. However, they can be formulated, if appropriate, in various ways, depending on the biological and/or chemical physical parameters which prevail. Possible formulations are, for example:

wettable powders (WP), emulsifiable concentrates (EC), aqueous solutions (SL), emulsions, sprayable solutions, oil- or water-based dispersions (SC), suspoemulsions (SE), dusting agents (DP), seed-dressing products, granules in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), ULV formulations, microcapsules, waxes or baits.

These individual types of formulation are known in principle and are described, for example, in:

Winnacker-Küchler, “Chemische Technologie” [Chemical Technology], Volume 7, C. Hauser Verlag Munich, 4th ed. 1986; van Falkenberg, “Pesticides Formulations”, Marcel Dekker N. Y., 2nd ed. 1972-73; K. Martens, “Spray Drying Handbook”, 3rd ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials, surfactants, solvents and other additives, are likewise known and are described, for example, in:

Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J.; H.v. Olphen, “Introduction to Clay Colloid Chemistry”, 2nd ed., J. Wiley & Sons, N.Y.; Marsden, “Solvents Guide”, 2nd ed., lnterscience, N.Y. 1950; McCutcheon's, “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Surface-Active Ethylene Oxide Adducts], Wiss. Verlagsgesell, Stuttgart 1967; Winnacker-Küchler, “Chemische Technologie”, Volume 7, C. Hauser Verlag Munich, 4th ed. 1986.

Based on these formulations, it is also possible to produce combinations with other pesticidally active compounds, fertilizers and/or growth regulators, for example in the form of a readymix or a tank mix. Wettable powders are preparations, uniformly dispersible in water, which contain, beside the active compound and in addition to a diluent or inert material, wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols, alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2′-dinaphthylmethane-6,6′-disulfonate.

Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons, with addition of one or more emulsifiers. As emulsifiers, the following can be used, for example: calcium salts of alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

Dusting agents are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth. Granules can be prepared either by atomizing the active compound onto adsorptive, granulated inert material or by applying active compound concentrates onto the surface of carriers such as sand or kaolinites, or of granulated inert material, by means of adhesives, for example polyvinyl alcohol or sodium polyacrylate, or alternatively mineral oils. Suitable active compounds can also be granulated in the fashion conventional for the preparation of fertilizer lgranules, if desired as a mixture with fertilizers.

In wettable powders, the concentration of active compound is, for example, from approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation components. In the case of emulsifiable concentrates, the concentration of active compound may be from approximately 5 to 80% by weight. Formulations in dust form comprise at most from 5 to 20% by weight of active compound, sprayable solutions from about 2 to 20% by weight. In the case of granules, the content of active compound depends partly on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc. are being used.

In addition, the abovementioned formulations of active compound comprise, if appropriate, the tackifiers, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers which are customary in each case.

The concentrates, which are in the commercially customary form, are if appropriate diluted in the customary manner for their use, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and some microgranules. Dust and granule preparations, and also sprayable solutions, are normally not diluted any further with other inert substances before being used.

The application rate required varies with the external conditions, such as temperature and humidity among others. It can fluctuate within wide limits, for example between 0.1 g/ha and 1.0 kg/ha or more of active compound, but is preferably between 0.1 g/ha and 0.3 kg/ha. Owing to the synergistic effects between Bt cotton and insecticide, particular preference is given to application rates of from 0.5 to 50 g/ha.

For pyrethroids (b), application rates of from 0.1 to 10 g/ha are preferred and particular preference is given to application rates of from 0.1 to 6.0 g/ha.

The active compounds according to the invention may be present in their commercially customary formulations, and in the application forms prepared from these formulations, as mixtures with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides.

Other preferred co-components for mixtures are

1. from the group of phosphorus compounds azamethiphos, azinphos-ethyl-, azinphosmethyl, bromophos, bromophosiethyl, cadusafos (F67825), chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenitriothion, fensulfothion, fenthion, fonofos, formothion, fosthiazate (ASC-66824), isozophos, isothioate, isoxathion, methacrifos, methidathion, salithion, mevinphos, naled, omethoate, oxydemeton-methyl, phenthoate, phorate, phosalone, phosfolan, phosphocarb (BAS-301), phosmet, phosphamidon, phoxim, pirimiphos, primiphos-ethyl, pirimiphos-methyl, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thiometon, triazophos, trichlorphon, vamidothion;

2. from the group of carbamates alanycarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, HCN-801, isoprocarb, methomyl, 5-methyl-m-cumenyl butyryl(methyl)carbamate, oxamyl, propoxur, thiodicarb, thiofanox, 1-methylthio(ethylideneamino) N-methyl-N-(morpholinothio)carbamate (UC 51717), triazamate;

3. from the group of carboxylic acid esters acrinathrin, allethrin, alphametrin, 5-benzyl-3-fuiylmethyl (E)-(1R)-cis, 2,2-di-methyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, beta-cyfluthrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, biphenthrin, (RS)-1-cyario-1-(6-phenoxy-2-pyridyl)-methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dirnethylcyclopropane-carboxylate (NCI 85193), cycloprothrin, cythithrin, cyphenothrin, empenthrin, esfenvalerate, fenfluthrin, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin (S-41311), pgrmethrin, phenothrin ((R) isomer), prallethrin, pyrethrins (naturally occurring products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin (TD-2344), transfluthrin, zeta-cypermethrin (F-56701);

4. from the group of amidines chlordimeform;

5. from the group of tin compounds cyhexatin;

6. others ABG-9008, acetamiprid, Anagrapha falcitera, AKD-1022, AKD-3059, ANS-118, Bacillus thuringiensis, Beauveria bassianeai, bensultap, bifenazate (D-2341), binapacryl, BJL-932, bromopropylates, BTG-504, BTG-505, buprofezin, camphechlor, cartap, chlorobenzilates, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthiophene (UBI-T 930), chlorfentezines, chromafenozides, (ANS-118), CG-216, CG-217, CG-234, A-184699, (2-naphthylmethyl) cyclopropanecarboxylate (Ro12-0470), cyromazin, diacloden (thiamethoxam), ethyl N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyl)-2-chloro-benzocarboximidate, DDT, dicofol, diflubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-ylidene)-2,4-xylidene, dinobuton, dinocap, diofenolan, DPX-062, emamcetin-benzoates (MK-244), endosulfan, ethiproles, (sulfethiproles), ethofenprox, etoxazoles (YI-5301), fenoxycarb, fluazuron, flumites, (flufenzines, SZI-121), 2-fluoro-5-(4-(4-ethoxyphenyl)4-methyl-1-pentyl)diphenyl ether (MTI 800), granulosis and nuclear polyhedrosis viruses, fenpyroximates, fenthiocarb, flubenzimines, flucycloxuron, flufenoxuron, fluferiprox (ICI-A5683), fluproxyfen, gamma-HCH, halofenocides (RH-0345), halofenprox (MTI-732), hexaflumuron (DE-473), hexythiazox, HOI-9004, hydramethylnon (AC 217300), lufenuron, indoxacarb (DPX-MP062), kanemites (AKD-2023), M-020, MIT446, ivermectin, M-020, methoxyfenocides (Intrepid, RH-2485), milbemectin, NC-196, neemgard, nitenpyram (TI-304), 2-nitromethyl-4,5-dihydro-6H-thiazine (DS 52618), 2-nitromethyl-3,4-dihydrothiazole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), pyriproxyfen (S-71639), NC-196, NC-1111, NNI-9768, novaluron (MCW-275), OK-9701, OK-9601, OK-9602, propargites, pymethrozines, pyridaben, pyrimidifen (SU-8801), RH-0345, RH-2485, RYI-210, S-1283, S-1833, SB7242, SI-8601, silafluofen, silomadines (CG-177), SU-9118, tebufenpyrad (MK-239), teflubenzuron, tetradifon, tetrasul, thiacloprid, thiocyclam, TI-435, tolfenpyrad (OMI-88), triflumuron, verbutin, vertalec (Mykotal), YI-5301.

The active compound content of the use forms prepared from the commercial formulations can be from 0.00000001 to 95% by weight, preferably between 0.00001 and 1% by weight, of active compound.

Owing to the synergistic effects with the Bt cotton plants and with one another, in particular mixtures of the active compounds used according to the invention can be employed in more dilute formulations.

Formulations of mixtures of pyrothroids and organophosphorus compounds contain correspondingly, for example, preferably from 0.05 to 0.01% by weight of pyrethroid and from 0.25 to 0.20% by weight of organophosphorus compound, particularly preferably from 0.01 to 0.001% by weight of pyrethroid and from 0.2 to 0.1% by weight of organophosphorus compound.

For mixtures of pyrethroids and endosulfan, preference is given to a ratio of from 0.05 to 0.01% by weight of pyrethroid to from 0.7 to 0.2% by weight of endosulfan, and particular preference is given to from 0.01 to 0.001% by weight of pyrethroid and from 0.35 to 0.2% by weight of endosulfan.

For mixtures of pyrethroids and Bacillus thuringiensis Bt, the values given above for pyrethroids apply, and the Bt proportion is preferably from 0.01 to 0.001, particularly preferably from 0.005 to 0.001, % by weight.

Mixtures of endosulfan and amitraz preferably contain from 0.35 to 0.2% by weight of endosulfan and from 0.6 to 0.2% by weight of amitraz.

In their commercial formulations, the active compounds used according to the invention can also be employed in combination with other fungicides which are known from the literature.

Suitable fungicides which are known from the literature are, for example, the following products:

aldimorph, andoprim, anilazine, azoxystrobin, azaconazole, BAS 450F, benalaxyl, benodanil, benomyl, bethoxazin, binapacyl, bion (CGA-245704), bitertanol, bromuconazole, buthiobate, captafol, captan, carbendazim, carboxin, carpropamides, CGA 173506, cymoxanil, cyproconazoles, cyprodinil, cyprofuram, diflumetorim, dichlofluanid, dichlomezin, diclobutrazol, diclocymet (S-2900), diclomezine, diethofencarb, difenconazole (CGA 169374), difluconazole, dimethirimol, dimethomorph, diniconazole, dinocap, dithianon, dodemorph, dodine, edifenfos, epoxiconazole, ethirimol, etridiazol, famoxadone, (DPX-JE874), fenarimol, fenazaquin, fenbuconazole, fenfuram, fenhexamid, fenpiclonil, fenpropidin, fenpropimorph, fentin acetates, fentin hydroxides, ferimzone (TF164), fluazinam, fluobenzimine, fludioxonil, flumetover (RPA403397), fluquinconazole, fluorimide, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetylaluminum, fuberidazole, furalaxyl, furconazole, furametpyr (S-82658), furmecyclox, guazatine, hexaconazole, imazalil, imibenconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, KNF 317, kresoximemethyl (BAS49OF), copper compounds such as Cu oxychloride, oxime-Cu, Cu oxides, mancozeb, maneb, mepanipyrim (KIF 3535), mepronil, metalaxyl, metalaxyl-M (CGA-329351), metconazole, methasulfocarb, methfuroxam, metominofen (SSF-126), mentominostrobin (fenominostrobin, SSF-126), MON 24000, MON6550, MON41100, myclobutanil, nabam, nitrothalidopropyl, nuarimol, ofurace, OK-9601, OK-9603, oxadixyl, oxycarboxin, paclobutrazole, penconazole, pencycuron, PP 969, polyoxins, probenazole, propineb, prochloraz, procymidon, propamocarb, propiconazole, prothiocarb, pyracarbolid, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, quinoxyfen (DE-795), rabenzazole, RH-7592, RH-7281, sulfur, spiroxamine, SSF-109, tebuconazole, tetraconazole, TTF 167, thiabendazole, thicyofen, thifluzamides (RH-130753), thiofanatemethyl, thiram, TM402, tolclofos-methyl, tolyfluanid, triadimefon, triadimenol, triazoxide, trichoderma, harzianum(DHF-471), tricyclazole, tridemorph, triflumizol, triforine, triflumizoles, (UCC-A815), triticonazoles, uniconazole, validamycin, vinchlozoline, XRD 563, zineb, sodium dodecylsulfonates, sodium dodecylsulfate, sodium C13-C15-alcohol ether sulfonate, sodium cetostearyl phosphate ester, dioctyl sodium sulfosuccinate, sodium isopropyl naphthalenesulfonate, sodium methylenebisnaphthalene sulfonate, cetyl-trimethyl-ammonium chloride, salts of long-chain primary, secondary or tertiary amines, alkylpropyleneamines, laurylpyrimidinium bromide, ethoxylated uaternized fatty amines, alkyldimethylbenzylammonium chloride and 1-ydroxyethyl-2-alkylimidazoline.

The abovementioned co-components are known active compounds, most of which are described in C. D. S. Tomlin, S. B. Walker, The Pesticide Manual, 11th edition (1997), British Crop Protection Council. The content of active compound of the use forms prepared from the commercial formulations can vary within wide ranges; the active compound concentration of the use forms can be from 0.0001 to 95% by weight of active compound, and is preferably between 0.0001 and 1% by weight. Such mixtures contain, for example, from 0.05 to 0.01% by weight of a pyrethroid and from 0.5 to 2% by weight of a fungicide, such as pyrazofos or prochloraz. The application is carried out in a customary manner adapted to the use forms.

The content of active compound of the use forms prepared from the commercial formulations can be from 0.00000001 to 95% by weight of active compound and is preferably between 0.00001 and 1% by weight.

In a preferred variant of the process according to the invention, the insecticidally active compound and a fungicide are applied together.

Application is carried out in a customary manner adapted to the use forms.

The process according to the invention is preferably suitable for application in the first (L1) larval stage, but preference is likewise given to application in later (L2 and/or L3) larval stages and/or in adult insects, in particular when controlling Lepidoptera.

For the purpose of the invention, the term “Bt cotton” is to be understood as cotton plants or crops which are genetically modified in such a way that they contain and express one or more genes from Bacillus thuringiensis which encode crystal proteins from the Cry family, see, for example, D. L. Prieto-Sansónor et al., J. Ind. Microbiol. & Biotechn. 1997, 19, 202 and 1997 BCPL Symposium Proceedings No. 68, 83-100).

Preference is given to genes encoding the proteins Cry1Aa, Cry1Ad, Cry1Ab, Cry1Ae, Cry1Ac, Cry1Fa, Cry1Fb, Cry1Ga, Cry1Gb, Cry1Da, Cry1Db, Cry1Ha, Cry1Hb, Cry1Ca, Cry1Cb, Cry1Ea, Cry1Eb, Cry1Ja, Cry1Jb, Cry1Bb, Cry1Bc, Cry1Bd, Cry1Ba, Cry11Ka, Cry11a, Cry1b, Cry7Aa, Cry7Ab, Cry9Ca, Cry9Da, Cry9Ba, Cry9Aa, Cry8Aa, Cry8Ba, Cry8Ca, Cry3Aa, Cry3Ca, Cry3Ba, Cry3Bb, Cry4Aa, Cry4Ba, Cry1OAa, Cry19Aa, Cry19Ba, Cry16Aa, Cry17Aa, Cry5Ab, Cry5Ba, Cry12Aa, Cry13Aa, Cry14Aa, Cry15Aa, Cry2Aa, Cry2Ab, Cry2Ac, Cry18Aa, Cry11Aa, Cry11Ba, Cyt1Aa, Cyt1Ab, Cyt1Ba, Cyt2Aa, Cyt2Ba, Cry6Aa, Cry6Ba.

Particular preference is given to Cry3Ca, Cryl Ab, Cry7Aa, Cry9C and CrylDa.

Likewise, particular preference is given to CrylAa, CrylAb, CrylAc, CrylB, CrylC, Cry2A, Cry3, Cry3A, Cry3C,Cry5 and Cry9C.

Very particular preference is given to the subfamilies Cryl and Cry9, in particular to Cry lA, CrylC, CrylF, and Cry9C.

Preference is furthermore given to using plants containing genes for a plurality of Bt proteins.

In addition to the expression of toxins from Bacillus thuringiensis (Bt) for insect resistance, the transgenic crop plants may also have other transgenic properties, for example further insect resistances (for example by expression of a protease or peptidase inhibitor, cf. WO-A-95/35031), herbicide resistances (for example against glufosinates or glyphosates by expression of the pat or bar gene) or else resistance against nematodes, fungi or viruses (for example by expression of a glucanase, chitinase), or may also be genetically modified in their metabolic properties, resulting in a qualitative and/or quantitative change of ingredients (for example by modification of the energy, carbohydrate, fatty acid or nitrogen metabolism or by metabolite streams which influence these).

Preference is given, for example, to Bt cotton plants which additionally have glufosinate or glyphosate resistance.

Bt cotton is known and, including methods for its preparation, described in idetail, for example, in U.S. Pat. No. 5,322,938; Prietro-Samsonór et al., J. Ind. Microbiol. & Biotechn. 1997, 19, 202, and H. Agaisse and D. Lereclus, J. Bacteriol. 1996, 177, 6027.

Bt cotton is furthermore commercially available in different varieties, for example under the name NuCOTN® from Deltapine (USA).

For the method according to the invention, preference is given to the following types of Bt cotton: NuCOTN33® and NuCOTN33B®).

Routes for preparing transgenic plants which, in comparison to naturally occurring plants, have modified properties, consist, for example, in the use of genetic engineering process (see, for example, Willmitzer L., 1993, Transgenic plants. In: Biotechnology, A Multivolume Comprehensive Treatise, Rehm et al. (eds.) Vol.2, 627-659, VCH Weinheim, Germany; D'Halluin et al., 1992, Biotechnology 10, 309-314, McCormick et al., Plant Cell Reports,1986, 5, 81-84; EP-A-0221044 and EP-A-0131624).

What is described is, for example, the preparation of genetically modified plants with respect to modifications of the hydrocarbon metabolism of the plant (for example WO 94/28146, WO 92/11376, WO 92/14827, WO 91/19806), resistances against certain herbicides, for example of the glufosinate type (cf., for example EP-A-0242236, EP-A-242246) or glyphosate type (for example WO 92/00377).

Numerous techniques of molecular biology which allow the preparation of novel transgenic plants having modified properties are known to the person skilled in the art; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker, Gene und Kione [Genes and clones], VCH Weinheim 2nd Edition, 1996 or Christou, Trends in Plant Science 1 (1996) 423-431).

In order to carry out such genetic manipulations, it is possible to introduce suitable nucleic acid molecules into plants or plant cells, for example by using suitable vectors which allow mutagenesis or a change in the sequence to occur by recombination of DNA sequences. Using the abovementioned standard processes, it is possible, for example, to exchange bases, to remove partial sequences or to add natural or synthetic sequences. It is also possible, for example, to replace the lnaturally occurring genes completely by heterologous or synthetic genes, ipreferably under the control of a promoter which is active in plant cells (“gene replacement”). To link the DNA fragments with each other, it is possible to attach adapters or linkers to the fragments.

Plant cells having a reduced activity of a gene product can be prepared, for example, by expressing at least one appropriate antisense-RNA, a sense-RNA to achieve a cosuppression effect, or by expressing at least one appropriately constructed ribozyme which specifically cleaves transcripts of the abovementioned gene product.

To this end, it is possible to employ both DNA molecules which comprise the entire coding sequence of the gene product including any flanking sequences that may be present, and DNA molecules which comprise only parts of the coding sequence, it being necessary for these parts to be long enough to cause an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product but which are not entirely identical.

When expressing nucleic acid molecules in plants, the synthesized protein can be localized in any desired compartment of the plant cells. However, to achieve localization in a certain compartment, it is, for example, possible to link the coding region with DNA sequences which ensure localization in a certain compartment or at a certain point of time (at a certain stage or chemically or biologically induced) (for example transit or signal peptides, time- or site-specific promoters). Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

Transgenic plant cells can be regenerated to whole plants using known techniques.

In this manner, it is possible to obtain transgenic plants which have modified properties by overexpression, suppression or inhibition of homologous (i.e. natural) genes or gene sequences or by expression of heterologous (i.e. foreign) genes or gene sequences.

The process according to the invention is suitable for controlling a large number of harmful organisms which occur, in particular, in cotton, in particular insects, arachnids and helminths, very particularly preferably insects and arachnids. The abovementioned pests include:

From the order of the Acarina, for example Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp.

From the order of the Isopoda, for example, Oniscus asselus, Armadium vulgar and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda for example, Geophilus carpophagus and Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Blatta orientalis, Peiplaneta americana, Leucophaea madeirae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Anoplura, for example, Phylloera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.

From the order of the Mallophaga, for example, Trichodectes pp. and Damalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis,

Thrips tabaci.

From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humui, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp and Psylla spp.

From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonela, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylloides chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrynchus assimilis, Hypera postica, Dermestes spp., Trogoderma, Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleaeand Tipula paludosa.

From the order of the Siphonaptera, for example, Xenopsylla cheopsis and Ceratophyllus spp.

From the order of the Arachnida, for example, Scorpio maurus and Latrodectus mactans.

From the class of Helminthen, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis as well as Fasciola.

The method according to the invention is preferably suitable for controlling insects from the orders Homoptera, preferably Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Myzus spp., Lepidoptera, preferably Agrotis spp., Heliothis spp., Mamestra brassicae, Prodinia litura, Spodoptera spp., Trichoplusia ni, and Coleoptera, preferably Anthonomus spp.

The method according to the invention is particularly preferably suitable for controlling insects from the class of the Lepidoptera, particularly preferably of Spodoptera, Agrotis, Heliothis, and very particularly preferably of Spodoptera littoralis, Agrotis segetum and Heliothis virescens.

Surprisingly, the method is also suitable for controlling harmful organisms which are resistant to individual classes of insecticides, such as pyrethroids, organophosphorus compounds or Bt.

The invention is illustrated in more detail by the examples, without limiting it thereby.

The contents of german patent application 198 25 333.8, whose priority is claimed by the present application, and the contents of the appended abstract, are incorporated herein specifically by way of reference; they are considered as part of the present description by way of citation:

EXAMPLE 1 Heliothis virescens

Seven-week-old cotton plants (common cotton, Vulkano®) and Bt cotton (NUCOTN 33B®), Delta Pine) were sprayed with the insecticides to be tested with the aid of a track sprayer (200 l/ha). After drying, plants were infected with 8 (L3) larvae of Heliothes virescens. Feeding damage and mortality were assessed after 2 and 4 days.

Test conditions: greenhouse, 23° C., 60% atmospheric humidity. All three active compounds showed a synergistic effect.

Compound 2 d 4 d g of active Feeding damage/mortality Feeding damage/mortality compound/ha Cotton Bt cotton Cotton Bt cotton Control 1 5 0 <1 0 7 0 1 75 Control 2 10 0 <1 25 15 0 1 88 Thiodan (endosulfan) EC33 525 0 100 <1 63 0 100 <1 88 175 3 63 <1 0 3 63 <1 75  58 5 0 <1 0 7 0 <1 75  19 10 0 <1 0 15 0 <1 88  6.5 10 0 <1 0 20 0 2 75 Decis (deltamethrin) EC 2.5  10 0 75 0 75 0 100 0 100  3.3 0 75 0 75 0 100 0 100  1.1 2 75 <1 75 2 100 <1 88  0.37 3 13 1 37 7 50 1 100  0.12 12 0 <1 37 12 25 1 88 Dipel (Bt) WP 3 100 <1 0 <1 13 1 100 1 100  33 1 0 <1 75 2 100 <1 100  11 1 0 <1 50 2 100 <1 100  3.7 4 0 <1 25 4 50 <1 100  1.2 6 0 <1 0 10 0 1 100

Decis and Dipel showed a synergistic effect.

EXAMPLE 2 Spodoptera littoralis

Three-month-old cotton plants (common cotton, Vulkano) and Bt cotton (NuCOTN 33B®) were sprayed with the insecticide to be tested with the aid of a track sprayer (200 l/ha). After drying, plants were infected with 10 (L3) larvae of Spodoptera littoralis.

Feeding damage and mortality were assessed after 2, 4 and 7 days.

Test conditions: (as for Example 1)

2d 4d 7d Compound Feeding damage/ Feeding damage/ Feeding damage/ active mortality mortality mortality compounds/ha Cotton Bt cotton Cotton Bt cotton Cotton Bt cotton Control l 8 10 8 0 15 10 12 0 20 10 35 0 Control 2 10 20 10 0 12 20 15 0 20 20 50 0 Control 3 6 20 10 0 15 20 10 0 20 20 45 0 Hostathion (triazophos) EC 40 125 3 100 1 100 3 100 1 100 3 100 1 100 42 8 20 2 40 10 30 2 60 15 30 2 100 14 5 10 3 40 10 20 5 40 15 20 15 50 5 5 40 7 10 6 40 8 20 10 40 25 20 1.5 5 30 6 0 8 30 10 0 20 30 25 0

A synergistic effect is clearly noticeable.

EXAMPLE 3 Spodoptera littoralis

Six-week-old cotton plants (common cotton, Vulkano®) and Bt cotton (NuCOTN 33B®) were sprayed with the insecticide to be tested with the aid of a track sprayer (200 l/ha). After drying, plants were infected with 10 (L3) larvae of Spodoptera littoralis.

Feeding damage and mortality were assessed after 2, 4 and 7 days.

Test conditions: (see Example 1)

2d 4d 7d Compound Feeding damage/ Feeding damage/ Feeding damage/ active mortality mortality mortality compounds/ha Cotton Bt cotton Cotton Bt cotton Cotton Bt cotton Control 1 8 0 10 0 20 0 20 0 60 0 50 0 Control 2 10 0 10 0 40 0 40 0 60 0 70 0 Control 3 10 0 10 0 25 0 50 0 70 0 40 0 Thiodan (endosulfan) EC 33 525 2 40 3 80 5 40 3 80 10 50 4 90 175 6 0 2 10 15 0 6 30 25 0 8 80 58 6 0 8 0 20 0 25 0 35 0 50 0 19 12 0 8 0 40 0 30 0 80 0 50 0 6.5 10 0 10 0 40 0 40 0 100 0 50 0

A synergistic effect is clearly noticeable.

EXAMPLE 4 Spodoptera littoralis

Seven-week-old cotton plants (common cotton, Felix®) and Bt cotton (NuCOTN 33B®) were sprayed with the insecticides to be tested with the aid of a track sprayer (200 l/ha). After drying, plants were infected with 10 (L3) larvae of Spodoptera littoralis.

Feeling damage and mortality were assessed after 2, 4 and 7 days.

Test conditions: (see Example 1)

2d 4d 7d Compound Feeding damage/ Feeding damage/ Feeding damage/ active mortality mortality mortality compounds/ha Cotton Bt cotton Cotton Bt cotton Cotton Bt cotton Control 1 12 0 10 0 20 0 20 0 40 0 50 0 Control 2 12 0 10 0 25 0 25 0 40 0 50 0 Control 3 12 0 10 0 30 0 30 0 40 0 40 0 Brestan (fentin) WP 60 1000 3 0 3 20 4 0 3 50 4 80 3 100 300 8 0 10 0 10 20 10 20 10 70 12 80 100 10 0 10 0 25 0 25 0 30 0 40 30 30 10 0 10 0 30 0 20 0 50 0 40 0 Piperonyl butoxide 1500 10 0 10 0 20 20 25 20 50 20 30 50 500 10 0 10 0 20 0 25 20 40 0 40 40 166 10 0 10 0 25 0 25 0 50 0 35 20 56 10 0 8 0 20 0 20 0 40 0 40 0 Vertimec (acemectin) EC 1.8 300 7 20 5 20 8 20 5 90 10 100 8 100 100 8 0 8 10 8 20 12 50 10 80 12 100 30 10 0 10 0 15 0 10 50 25 20 10 90 10 10 0 8 0 30 0 12 30 50 0 30 70

A synergistic effect is clearly noticeable.

EXAMPLE 5 Spodoptera lettoralis

Five-week-old cotton plants (common cotton, Vulkano®) and Bt cotton (NuCOTN 33B®)were sprayed with the insecticides to be tested with the aid of a track layer (200 l/ha). After drying, plants were infected with 10 (L3) larvae of Spodoptera littoralis.

Feeding damage and mortality were assessed after 2, 4 and 7 days.

Test conitions: (see Example 1)

2d 4d 7d Compound Feeding damage/ Feeding damage/ Feeding damage/ active mortality mortality mortality compounds/ha Cotton Bt cotton Cotton Bt cotton Cotton Bt cotton Control 10 0 10 0 35 0 15 0 50 0 20 0 Decis EC 2.5 30 0 80 1 100 0 100 1 100 0 100 1 100 10 1 90 3 70 1 100 3 80 1 100 8 100 3 5 20 5 70 25 20 6 80 40 20 8 100 1 10 10 8 10 25 10 12 10 40 10 25 10 Thiodan EC33 1000 1 90 0 80 1 100 0 100 1 100 0 100 300 4 40 0 80 5 40 0 80 8 40 0 100 100 5 40 3 60 10 40 6 60 20 40 10 60 Decisdan EC 0.5 (5 + 350 g/l) 30 + 2100 0 100 0 100 0 100 0 100 0 100 0 100 10 + 700 0 100 0 100 0 100 0 100 0 100 0 100 3 + 210 1 90 0 100 2 90 0 100 2 90 0 100 1 + 70 5 30 5 60 15 30 12 60 25 30 25 60 Decisdan EC 0.5 (5 + 300 g/l) 30 + 2100 0 100 0 100 0 100 0 100 0 100 0 100 10 + 700 0 100 0 80 0 100 0 100 0 100 0 100 3 + 210 1 90 1 90 1 90 3 90 1 90 5 90 1 + 70 5 50 3 60 10 50 8 60 25 50 15 60

Decis, Thiodan and Decisdan (5+350 g/l) showed a synergistic effect.

Example 6 Agrotis segetum

Eight-week-old cotton plants (common cotton, Felix®) and Bt cotton (NuCOTN 33®) were sprayed with the insecticides to be tested with the aid of a track sprayer (200 l/ha). After drying, plants were infected with 10 (L3) larvae of Agrotis segetum.

Feeding damage and mortality were assessed after 2, 4 and 7 days.

Test conditions: (see Example 1)

Compound 2 d 4 d active Feeding damage/mortality Feeding damage/mortality compounds/ha Cotton Bt cotton Cotton Bt cotton Control 1 3 0 3 0 10 0 4 0 Control 2 0 0 3 0 10 0 3 0 Piperonyl butoxide 3000 1 80 0 80 1 90 0 100 1000 1 30 0 30 2 60 1 90  300 0 50 1 60 2 60 1 90 Vertimec EC (avamectin)   1.8  300 0 40 1 80 3 60 2 100  100 0 50 1 90 1 80 1 90  30 1 10 1 0 1 10 1 20

A synergistic effect is clearly noticeable.

EXAMPLE 7 Agrotis segetum

Seven-week-old cotton plants (common cotton, Felix®) and Bt cotton (NUCOTN 33B®)) were sprayed with the insecticide to be tested with the aid of a track sprayer (200 l/ha). After drying, plants were infected with 10 (L3) larvae of Agrotis segetum.

Feeding damage and mortality were assessed after 2, 4 and 7 days.

Test conditions: (see Example 1)

2d 4d 7d Compound Feeding damage/ Feeding damage/ Feeding damage/ active mortality mortality mortality compounds/ha Cotton Bt cotton Cotton Bt cotton Cotton Bt cotton Control 1 10 0 35 0 10 0 40 0 10 0 50 0 Control 2 40 0 10 0 50 0 20 0 50 0 20 0 Control 3 20 0 20 0 30 0 30 0 40 0 35 0 Control 4 30 0 30 0 40 0 40 0 40 0 45 0 Decis (deltamethrin) EC2.5 10 1 60 0 50 2 70 0 90 2 80 0 100 3.3 0 0 0 40 3 30 0 50 3 30 0 50 1.1 2 0 0 20 2 20 0 30 3 20 0 30 0.37 3 0 10 20 5 20 15 20 5 10 15 20 0.12 2 0 3 0 5 0 0 0 5 0 0 0

A synergistic effect is clearly noticeable. 

What is claimed is:
 1. A method for controlling harmful organisms in genetically modified cotton plants which contain a gene derived from Bacillus thuringiensis which encodes and expresses an insecticidally active protein, which comprises applying an insecticidally effective amount of one or more compounds from the following groups a-f to the plants, to their seeds or propagation stock and/or to the area in which they are cultivated: a) Organophosphorus compounds: triazophos (726), monocrotophos (502), methamidophos (479), chlorpyrifos (137), parathion (551), acephate (4), profenofos (594), malathion (448), heptenophos (395); b) Pyrethroids: tralomethrin (718), cypermethrin (183), cyhalothrin (179), lambdacyhalothrin (180), deltamethrin (204), fenvalerates (319), (alpha)-cypermethrin (183/184), cyfluthrin (176), fenpropathrin (312), etofenprox (292); c) Carbamates: aldicarb (16), bendiocarb (56), carbaryl (106), carbofuran (109), formetanates (369), pirimicarb (583) d) Biopesticides: Bacillus thuringiensis (46, 47), granuloses and nuclear polyhedrosis viruses, Beauveria bassiana (52), Beauveria brogniartii (53), baculoviruses, such as Autographa california; e) Others: endosulfan (270), abamectin (1), XDE-105 (754), diafenthiuron (208), fipronil (323), chlorfenapyr (123), tebufenocides (679), fenazaquin (301), imidacloprid (418), triazamates (724), fentin (317), amitraz (22), MK-242 f) 4-Haloalkyl-3heterocyclylpyridines and 4haloalkyl-5-heterocyclylpyrimidines of the formula (1), if appropriate also in the form of their salts,

 where the symbols and indices have the following meanings: Y is halo-C₁-C₆-alkyl; X is CH or N; m is 0 or 1; Q is a 5-membered heterocycic group

 in which a) X¹ = W, X² = NR^(a), X³ = CR^(b)R¹ or b) X¹ = NR^(a), X² = CR^(b)R¹, X³ = W or c) X¹ = V, X² = CR^(a)R¹, X³ = NR^(b) or d) X¹ = V, X² = CR^(a)R², X³ = CR^(b)R³ or e) X¹ = V, X² = CR⁴R⁵, X³ = CR⁶R⁷ or f) X¹ = NR^(a), X² = CR^(b)R¹ , X³ = Nr⁸;

R^(a) and R^(b) together are a bond V is oxygen, sulfur or NR⁹; W is oxygen or sulfur; R¹ is hydrogen, (C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, where the six last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)NR¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)R¹⁰—NR¹⁰ ₂, —C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—N[C(═W)R¹⁰]₂, —N[(C═W)R¹⁰]—NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰[(C═W)WR¹⁰], —NR¹⁰—R¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —SO₂NR¹⁰ ₂, —NR¹⁰SO₂R¹⁰, —SO₂OR¹⁰, —OSO₂R¹⁰, OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —SeR¹⁰, —PR¹⁰ ₂, —P(═W)R¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, aryl and heterocyclyl, the two last-mentioned radicals optionally being substituted by one or more radicals from the group  (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈) cycloalkenyl, (C₆-C₈)-cycloalkynyl,  (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —SOR¹⁰,  —SO₂R¹⁰, nitro, cyano and hydroxyl, aryl, which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl, where these six abovementioned radicals are optionally substituted by one or more radicals from the group  halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰,  —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰, halogen, cyano, nitro, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, SiR¹⁰ ₃, —PR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂ and —PW₃R¹⁰ ₂, heterocyclyl, which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl, where the six abovementioned radicals are optionally substituted by one or more radicals from the group  cyano, nitro, halogen, —C(═W)R¹⁰, —C(═W)OR¹⁰,  —C(═W)NR¹⁰ ₂, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂,  —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰,  —SOR¹⁰ and —SO₂R¹⁰, halogen, cyano, nitro, —C(═W)R¹⁰, C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰, —SO₂R¹⁰, —C(═W)R¹⁰, —C(═NOR¹⁰)¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂, —C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—NC(═W)R¹⁰ ₂, —N(C═W)R¹⁰—NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—N¹⁰[(C═W)WR¹⁰], —NR¹⁰—NR¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —SO₂NR¹⁰ ₂, —NR¹⁰SO₂R¹⁰, —SO₂OR¹⁰, —OSO₂R¹⁰, —SC(═W)R¹⁰, —SC(═W)OR¹⁰, —SC(═W)R¹⁰, —PR¹⁰ ₂, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, SiR¹⁰ ₃ or halogen; R² and R³independently of one another have the definitions given in R¹; R² and R³ together form a 5- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹; R⁴ and R⁶ independently of one another have the definitions given in R¹; R⁴ and R⁶ together form a 4- to 7-membered ring which may be partially or fully unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, the oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹; R⁵ and R⁷ independently of one another are hydrogen, (C₁-C₂₀)-alkyl, (C₂-C₂₀)-alkenyl, (C₂-C₂₀)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl, where the six last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, —C(═W)R¹⁰, —C(═NOR¹⁰,)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —N¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰C(═W)OR¹⁰, —C(═W)NR¹⁰—NR¹⁰ ₂, —C(═W)NR¹⁰—NR¹⁰[C(═W)R¹⁰], —NR¹⁰—C(═W)NR¹⁰ ₂, —NR¹⁰—NR¹⁰C(═W)R¹⁰, —NR¹⁰—N[C(═W)R¹⁰]₂], —N[(C═W)R¹⁰]—NR¹⁰ ₂, —NR¹⁰—NR¹⁰[(C═W)R¹⁰], —NR¹⁰—NR¹⁰ [(C═W)WR¹⁰], —NR¹⁰—NR¹⁰[(C═W)NR¹⁰ ₂], —NR¹⁰(C═NR¹⁰)R¹⁰, —NR¹⁰(C═NR¹⁰)NR¹⁰ ₂, —O—NR¹⁰ ₂, —O—NR¹⁰(C═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —SeR¹⁰, —PR¹⁰ ₂, —P(═W)R¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂, —PW₃R¹⁰ ₂, aryl and heterocyclyl, of which the two mentioned last are optionally substituted by one or more radicals from the group  (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₆-C₈)-cycloalkynyl,  (C₁-C₆)-haloalkyl, (C₂-C₆)-haloalkenyl, (C₂-C₆)-haloalkynyl, halogen, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃,  —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —SOR¹⁰,  —SO₂R¹⁰, nitro, cyano and hydroxyl, aryl, which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl, where these six mentioned radicals are optionally substituted by one more radicals from the group  halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰,  —C(═W)NR¹⁰ ₂, OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and  —SO₂ R¹⁰, halogen, cyano, nitro, —C(═W)R¹⁰, —C(═NOR¹⁰,)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OC(═W)OR¹⁰, —NR¹⁰C(═W)R¹⁰, —N[C(═W)R¹⁰]₂, —NR¹⁰ C(═W)OR¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SiR¹⁰ ₃, —PR¹⁰ ₂, —SOR¹⁰, —SO₂R¹⁰, —PW₂R¹⁰ ₂ and —PW₃R¹⁰ ₂, pyridyl, which is optionally substituted by one or more radicals from the group (C₁-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl and (C₆-C₈)-cycloalkynyl, where the six abovementioned radicals are optionally substituted by one or more radicals from the group  cyano, nitro, halogen, —C(═W)R¹⁰, —C(═W)OR¹⁰,  —C(═W)NR¹⁰ ₂, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and  —SO₂R¹⁰, halogen, cyano, nitro, —C(═W)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂, —OC(═W)R¹⁰, —OR¹⁰, —NR¹⁰ ₂, —SR¹⁰, —SOR¹⁰ and —SO₂R¹⁰, —C(═W)R¹⁰, —C(═NOR¹⁰)R¹⁰, —C(═NNR¹⁰ ₂)R¹⁰, —C(═W)OR¹⁰, —C(═W)NR¹⁰ ₂ or halogen; R⁴ and R⁵ together form a 4- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹; R⁴ and R⁵ together form one of the groups ═O, ═S or ═N—R⁹; R⁶ and R⁷ together form a 5- to 7-membered ring which may be partially unsaturated and may be interrupted by one or more atoms from the group nitrogen, oxygen and sulfur, oxygen atoms not being directly adjacent to one another, and the ring optionally being substituted by one or more, but at most 5, radicals R¹; R⁶ and R⁷ together form one of the groups ═O, ═S or ═N-R⁹; R⁸ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl, where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl(C₁-C₄)-alkoxy, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄—C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)-mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbornyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, ((C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkylthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalkylsulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfonyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfonyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl -(C₄-C₈)-cycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, arylcarbamoyl, aroyl, aroyloxy, aryloxycarbonyl, arl-(C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl, of which the nineteen last-mentioned radicals are optionally substituted in their cyclic moiety by one or more substituents from the group  halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio, (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl and (C₁-C₄)-alkanoyl, aryl, which is optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, carbamoyl, (C₁-C₆)-mono- or dialkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₃-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆) alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino and (C₄-C₈)-halocycloalkenylamino, —C(═W)R¹¹, OR¹¹ or NR¹¹ ₂; R⁹ is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, where the nine last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆) alkynyloxy and (C₁-C₆)-haloalkyloxy; R¹⁰ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₈)-cycloalkyl, (C₄-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyl, where the fourteen last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-halocycloalkoxy, (C₄-C₈)-halocycloalkenyloxy, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkoxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkoxy, (C₃-C₈)-cyloalkyl-(C₂-C₄)-alkenyloxy, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenyloxy, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkoxy, (C₂-C₆)-alkynyl -(C₃-C₈)cycloalkoxy, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenyloxy, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenyloxy, (C₁-C₄)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₄)-alkoxy-(C₂-C₆)-alkenyloxy, carbamoyl, (C₁-C₆)mono- or dialkylcarbamoyl, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₃-C₈)mono- or dicycloalkylcarbamoyl, (C₁-C₆)-alkoxycarbonyl, (C₃-C₈)-cycloalkoxycarbonyl, (C₁-C₆)-alkanoyloxy, (C₃-C₈)-cycloalkanoyloxy, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₃-C₈)-cycloalkaneamido, (C₃-C₈)-cycoalkyl-(C₁-C₄)-alkaneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₄-C₈)-halocycloalkenylthio, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylthio, (C₃-C₈)-cyloalkyl-(C₂-C₄)-alkenylthio, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylthio, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylthio, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylthio, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylthio, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₄)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsulfinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfinyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfinyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfinyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfinyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfinyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆)-alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-cycloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylsulfonyl, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylsulfonyl, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkenylsulfonyl, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylsulfonyl, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylsulfonyl, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)-haloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkamino, (C₄-C₈)-halocycloalkenylamino, (C₃-C₈)-cycloalkyl-(C₁-C₄)-alkylamino, (C₄-C₈)-cycloalkenyl-(C₁-C₄)-alkylamino, (C₃-C₈)-cycloalkyl-(C₂-C₄)-alkenylamino, (C₄-C₈)-cycoalkenyl-(C₁-C₄)-alkenylamino, (C₁-C₆)-alkyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkenyl-(C₃-C₈)-cycloalkylamino, (C₂-C₆)-alkynyl-(C₃-C₈)-cycloalkylamino, (C₁-C₆)-alkyl-(C₄-C₈)-cycloalkenylamino, (C₂-C₆)-alkenyl-(C₄-C₈)-cycloalkenylamino, (C₁-C₆)-trialkylsilyl, aryl, aryloxy, arylthio, arylamino, aryl-(C₁-C₄)-alkoxy, aryl-(C₂-C₄)-alkenyloxy, aryl-(C₁-C₄)-alkylthio, aryl-(C₂-C₄)-alkenylthio, aryl-(C₁-C₄)-alkylamino, aryl-(C₂-C₄)-alkenylamino, aryl-(C₁-C₆)-dialkylsilyl, diaryl-(C₁-C₆)-alkylsilyl, triarylsilyl and 5- or 6-membered heterocyclyl, where the cyclic moiety of the fourteen last-mentioned radicals is optionally substituted by one or more radicals from the group  halogen, cyano, nitro, amino, hydroxyl, thio, (C₁-C₄)-alkyl,  (C₁-C₄)-haloalkyl, (C₃-C₈)-cycloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-haloalkylthio,  (C₁-C₄)-alkylamino, (C₁-C₄)-haloalkylamino, formyl and (C₁-C₄)-alkanoyl, aryl, 5- or 6-membered heteroaromatic, where the two last-mentioned radicals are optionally substituted by one or more radicals from the group halogen, cyano, nitro, hydroxyl, thio, amino, formyl, (C₁-C₆)-alkoxy, (C₂-C₆)-alkenyloxy, (C₂-C₆)-alkynyloxy, (C₁-C₆)-haloalkyloxy, (C₂-C₆)-haloalkenyloxy, (C₂-C₆)-haloalkynyloxy, (C₃-C₈)-cycloalkoxy, (C₄-C₈)-cycloalkenyloxy, (C₃-C₈)-haloyloalkoxy, (C₄-C₈)-halocyclalkenyloxy, carbamoyl, (C₁-C₆)-mono- or diaklylcarbamoyl, (C₁-C₆)-aklocycarbonyl, (C₁-C₆)-alkanoyloxy, (C₁-C₆)-mono- or dihaloalkylcarbamoyl, (C₁-C₆)-haloalkoxycarbonyl, (C₁-C₆)-haloalkanoyloxy, (C₁-C₆)-alkaneamido, (C₁-C₆)-haloalkaneamido, (C₂-C₆)-alkeneamido, (C₁-C₆)-alkylthio, (C₂-C₆)-alkenylthio, (C₂-C₆)-alkynylthio, (C₁-C₆)-haloalkylthio, (C₂-C₆)-haloalkenylthio, (C₂-C₆)-haloalkynylthio, (C₃-C₈)-cycloalkylthio, (C₄-C₈)-cycloalkenylthio, (C₃-C₈)-halocycloalkthio, (C₄-C₈)-halocycloalkenylthio, (C₁-C₆)-alkylsulfinyl, (C₂-C₆)-alkenylsulfinyl, (C₂-C₆)-alkynylsulfinyl, (C₁-C₆)-haloalkylsulfinyl, (C₂-C₆)-haloalkenylsulfinyl, (C₂-C₆)-haloalkynylsulfinyl, (C₃-C₈)-cycloalkylsulfinyl, (C₄-C₈)-cycloalkenylsufinyl, (C₃-C₈)-halocycloalksulfinyl, (C₄-C₈)-halocycloalkenylsulfinyl, (C₁-C₆)-alkylsulfonyl, (C₂-C₆)-alkenylsulfonyl, (C₂-C₆) alkynylsulfonyl, (C₁-C₆)-haloalkylsulfonyl, (C₂-C₆)-haloalkenylsulfonyl, (C₂-C₆)-haloalkynylsulfonyl, (C₃-C₈)-cycloalkylsulfonyl, (C₄-C₈)-haloalkenylsulfonyl, (C₃-C₈)-halocycloalksulfonyl, (C₄-C₈)-halocycloalkenylsulfonyl, (C₁-C₆)-alkylamino, (C₂-C₆)-alkenylamino, (C₂-C₆)-alkynylamino, (C₁-C₆)aloalkylamino, (C₂-C₆)-haloalkenylamino, (C₂-C₆)-haloalkynylamino, (C₃-C₈)-cycloalkylamino, (C₄-C₈)-cycloalkenylamino, (C₃-C₈)-halocycloalkylamino and (C₄-C₈)-haloycloalkenylamino; R¹¹ is (C₁-C₁₀)-alkyl, haloalkyl, aryl, which is optionally substituted by one or more radicals from the group halogen, cyano, nitro, (C₁-C₄)-alkoxy, (C₁-C₄)-alkyl, amino, (C₁-C₄)-monoalkylamino and (C₁-C₄)-dialkylamino, N¹⁰ ₂, OR¹⁰ or SR¹⁰.
 2. The method as claimed in claim 1, wherein a compound from the group consisting of the organophosphorus compounds, pyrethroids, corbamates, endosulfan, fipronil, abamectin, piperonyl butoxixde, XDE-105 and Bacilllus thuringensis is used.
 3. The method as claimed in claim 2, wherein a compound from the group consisting of triazaphos, endosulfan, deltamethrin, fipronil, abamectin, piperonyl butoxide and Bacillus thuringiensis is used.
 4. The method as claimed in claim 1, wherein a mixture of two or more of the insecticidally active compounds is used.
 5. The method as claimed in claim 1, wherein the insecticidally active compound is applied at an application rate of from 0.001 to 0.3 kg/ha.
 6. The method as claimed in claim 1, wherein the insecticidally active compound is employed as a from 0.00001 to 1% by weight strength formulation.
 7. The method as claimed in claim 1, wherein the insecticidally active Bt-protein in the cotton plant is a crystal protein from the subfamily Cryl or IX.
 8. The method as claimed in claim 1, wherein cotton plants are used which are glufosinate- or glyphosate-resistant.
 9. The method as claimed in claim 1, wherein the harmful organisms are insects which belong to the orders Homoptera, Lepidoptera and/or Coleoptera.
 10. The method as claimed in claim 1, wherein the insecticidally active compound is used against larvae in the L1 stage.
 11. The method as claimed in claim 1, wherein the insecticidally active compound is used against larvae in the L2 and/or L3 stage and/or against adult animals.
 12. The method as claimed in claim 1, wherein, in addition to one or more insecticidally active compounds from the group a-f, one or more other insecticidally, fungicidally or herbicidally active compounds are employed.
 13. The method as claimed in claim 7, wherein the insecticidally active protein in the cotton plant is Cry3Ca, CrylAb, Cry7Aa, Cry9C and CrylDa.
 14. The method as claimed in claim 7, wherein the insecticidally active protein in the cotton plant is CrylAa, CrylAb, CrylAc, CrylB, CrylC, Cry2A, Cry3, Cry3A, Cry3C, Cry5,Cry9C.
 15. The method of claim 1, wherein the compound comprises triazophos. 